Methanol → HCID 834084, compound

HRID 1153966Notes

Reaction equation

HRID 1153966 reaction equation
CO.[BH4-].[Na+].[CH:5]1([N:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1.O>C(Cl)Cl>[F:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][NH:10][CH:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 13201287HCID 13201287, compound

Product 1

HCID 834084HCID 834084, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

160 ml of methanol are added to 18.2 g of sodium borohydride. 90.7 g of 4-fluorobenzaldehyde-cyclopentylimide are added dropwise at 10°-15° C., while cooling with ice and stirring, and the mixture was then stirred for 1.5 hours at room temperature. 120 ml of H2O and 150 ml of methylene chloride were then added, the methylene chloride phase was separated off, and the aqueous phase was further extracted twice with CH2Cl2. The combined methylene chloride phases were washed with water and dried with Na2SO4, and the solvent was stripped off in vacuo. Distillation of the residue under a medium vacuum gave 85.9 g of N-4-fluorobenzyl-N-cyclopentylamine of boiling point 106° C. 0.25 bar.

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe mixture was then stirred for 1.5 hours at room temperature
  3. customthe methylene chloride phase was separated off
  4. extractionthe aqueous phase was further extracted twice with CH2Cl2
  5. washThe combined methylene chloride phases were washed with water
  6. dry with materialdried with Na2SO4
  7. distillationDistillation of the residue under a medium vacuum

Sources & evidence

ORD record
ord-9688974949384867b5dbbc553983ca80
Source dataset
uspto-grants-1984_12
Patent number
US04487783

Reaction notes

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