Chloroform → HCID 14405646, compound

HRID 1110766Notes

Reaction equation

HRID 1110766 reaction equation
N1([CH2:7][N:8]2[CH2:20][CH2:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[NH:11][C:10]=3[CH2:9]2)CCCCC1.C([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[CH:37](Cl)(Cl)Cl>>[C:28]([N:23]1[CH2:24][CH2:25][CH:37]([CH2:7][N:8]2[CH2:20][CH2:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[NH:11][C:10]=3[CH2:9]2)[CH2:27][CH2:26]1)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 6212Chloroform2×HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22154185HCID 22154185, compound

Product 1

HCID 14405646HCID 14405646, compound

Conditions

Temperature
20 °C

Procedure

2.7 g (10 mmol) of 2-[(piperidyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, 30 ml of chloroform and 1.6. ml (11 mmol) of triethylamine are introduced under an argon atmosphere into a Keller flask. 1.546 g (11 mmol) of benzoyl chloride dissolved in 100 ml of chloroform are added, and the mixture is stirred at 20° C. for 48 H. The solvent is evaporated off under reduced pressure, and the residue is taken up with water, filtered off, dissolved in ethyl acetate and treated with activated charcoal. After filtration, the solvent is evaporated off under reduced pressure and the residue crystallized in isopropyl ether and recrystallized in acetonitrile. 1.8 g of white solid are obtained. Melting point: 161.5°-163.5° C.

Workup

  1. additionare added
  2. customThe solvent is evaporated off under reduced pressure
  3. filtrationfiltered off
  4. dissolutiondissolved in ethyl acetate
  5. additiontreated with activated charcoal
  6. filtrationAfter filtration
  7. customthe solvent is evaporated off under reduced pressure
  8. customthe residue crystallized in isopropyl ether
  9. customrecrystallized in acetonitrile

Sources & evidence

ORD record
ord-3600930fbd1d40589682317d8851b1c2
Source dataset
uspto-grants-1990_12
Patent number
US04977159

Reaction notes

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