Sodium Hydroxide → HCID 12804790, compound

HRID 1106052Notes

Reaction equation

HRID 1106052 reaction equation
Cl.[C:2]1([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2([OH:20])[CH2:19][CH2:18][NH:17][CH2:16]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:21].[Na+]>CO.O.CCOCC>[C:8]([N:17]1[CH2:18][CH2:19][C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([OH:20])[CH2:16]1)(=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 12804789HCID 12804789, compound

Product 1

HCID 12804790HCID 12804790, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 5.0 g of 3-(α-phenyl-2-tolyl)-3-pyrrolidinol hydrochloride, Example 14, in 40 ml of methanol is diluted with water until a solution forms. The solution is treated with an excess of a 5% sodium hydroxide solution and then the methanol removed on a rotary evaporator leaving a suspension. The suspension is diluted with 50 ml of water and extracted successively with a 100 ml and a 20 ml portion of chloroform. The combined chloroform extracts are washed once with 50 ml of a 5% sodium hydroxide solution and twice with 50 ml portions of water and dried and the chloroform removed. The residue is subjected to azeotropic distillation with benzene and then dried in vacuo at 40° C. for 2 hours before being suspended in 30 ml of warmed chloroform containing 2.2 g of triethylamine. To this suspension is added dropwise 2.60 g of benzoyl chloride. After total addition, the resulting solution is stirred for 2 hours and then permitted to stand for 48 hours. The solution is diluted with 30 ml of chloroform, washed successively with a 50 ml portion of water and similar amount of a 5% sodium hydroxide and dried and the solvent removed leaving a tacky foam. The foam is dissolved in 60 ml of ether (warming may be required), and the solution filtered through glass wool. A precipitate forms which is collected by suction filtration and dried in vacuo at ambient temperature leaving a colorless solid, mp 113°-116° C. of 1-benzoyl-3-(α-phenyl-2-tolyl)-3-pyrrolidinol.

Workup

  1. customthe methanol removed on a rotary evaporator
  2. customleaving a suspension
  3. extractionextracted successively with a 100 ml
  4. washThe combined chloroform extracts are washed once with 50 ml of a 5% sodium hydroxide solution and twice with 50 ml portions of water
  5. customdried
  6. customthe chloroform removed
  7. distillationThe residue is subjected to azeotropic distillation with benzene
  8. customdried in vacuo at 40° C. for 2 hours
  9. additionTo this suspension is added dropwise 2.60 g of benzoyl chloride
  10. additionAfter total addition
  11. waitto stand for 48 hours
  12. additionThe solution is diluted with 30 ml of chloroform
  13. washwashed successively with a 50 ml portion of water and similar amount of a 5% sodium hydroxide
  14. customdried
  15. customthe solvent removed
  16. customleaving a tacky foam
  17. filtrationthe solution filtered through glass wool
  18. filtrationA precipitate forms which is collected by suction filtration
  19. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-6f7c7a922123480b95786a578970f9bf
Source dataset
uspto-grants-1982_01
Patent number
US04311703

Reaction notes

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