Benzoyl chloride → HCID 12798185, compound

HRID 1380629Notes

Reaction equation

HRID 1380629 reaction equation
[CH:1]([NH:4][CH2:5][CH:6]1[CH2:10][O:9][C:8]2([CH:18]([Br:19])[CH2:17][CH2:16][C:15]3[N:14]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH:13]=[CH:12][C:11]2=3)[O:7]1)([CH3:3])[CH3:2].[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>N1C=CC=CC=1>[CH:1]([N:4]([CH2:5][CH:6]1[CH2:10][O:9][C:8]2([CH:18]([Br:19])[CH2:17][CH2:16][C:15]3[N:14]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH:13]=[CH:12][C:11]2=3)[O:7]1)[C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 12946401HCID 12946401, compound

Product 1

HCID 12798185HCID 12798185, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4'-isopropylaminomethyl-1-p-toluenesulfonyl-5-bromo-4,5,6,7-tetrahydroindole-4-spiro-2'-[1,3]dioxolane (100 parts) dissolved in pyridine (343 parts) is prepared and placed in a three necked flask equipped with a stirrer and a thermometer. Benzoyl chloride (35 parts) is added dropwise at 0° C. to 5° C. After standing at room temperature for 14 hours, the reaction mixture is evaporated to remove pyridine at below 70° C. Obtained residue is dissolved in a dichloromethane (300 parts) and washed three times with water (50 parts). Aqueous washings are combined and washed with dichloromethane (50 parts). Dichloromethane solution and dichloromethane washing are combined, washed with water (30 parts), are dried over anhydrous sodium sulfate. After 1 hour, the drying agent is removed by filtration, and obtained filtrate is concentrated to dryness under reduced pressure. Obtained residue (132 parts) is dissolved in dichloromethane (270 parts), allowed to stand for half an hour with active charcoal (30 parts), and filtered through Florisil filter-bed. The resulting filtrate is concentrated under reduced pressure to dryness at below 30° C. and the obtained residue is triturated in a small amount of a mixture of benzene and dichloromethane to give amorphous powder. The product is collected by filtration and dried to give 4'-(N-isopropyl-N-benzoylaminomethyl)-1-p-toluenesulfonyl-5-bromo-4,5,6,7-tetrahydroindole-4-spiro-2'-[1,3]dioxolane (111 parts) in 91.5% yield.

Workup

  1. customis prepared
  2. customequipped with a stirrer
  3. customthe reaction mixture is evaporated
  4. customto remove pyridine at below 70° C
  5. dissolutionObtained residue is dissolved in a dichloromethane (300 parts)
  6. washwashed three times with water (50 parts)
  7. washwashed with dichloromethane (50 parts)
  8. washwashed with water (30 parts)
  9. dry with materialare dried over anhydrous sodium sulfate
  10. waitAfter 1 hour
  11. customthe drying agent is removed by filtration
  12. customobtained filtrate
  13. concentrationis concentrated to dryness under reduced pressure
  14. dissolutionObtained residue (132 parts) is dissolved in dichloromethane (270 parts)
  15. waitto stand for half an hour with active charcoal (30 parts)
  16. filtrationfiltered through Florisil
  17. filtrationfilter-bed
  18. concentrationThe resulting filtrate is concentrated under reduced pressure to dryness at below 30° C.
  19. customthe obtained residue is triturated in a small amount of a mixture of benzene and dichloromethane
  20. customto give amorphous powder
  21. filtrationThe product is collected by filtration
  22. customdried

Sources & evidence

ORD record
ord-1997330764d349428b60459e5c1e1586
Source dataset
uspto-grants-1986_04
Patent number
US04582905

Reaction notes

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