Methanol → 2-[(4-Chlorophenyl)methyl]azepane

HRID 27428

Reaction equation

HRID 27428 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:8]=2)=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>Cl>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 233428152-(4-chlorobenzyl)-4,5,6,7-tetrahydro-3H-azepine

Product 1

HCID 39338092-[(4-Chlorophenyl)methyl]azepane

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

Dissolve the thus-obtained 2-(4-chlorobenzyl)-4,5,6,7-tetrahydro-3H-azepin in diluted hydrochloric acid (pH~5) and mix it with 200 ml of methyl alcohol. Add 7 g of sodium borohydride in small portions within 20 minutes, keeping the pH-value constant by occasional addition of hydrochloric acid. Stir for 1 hour, render alkaline with caustic soda solution and extract with dichlormethane. Dry the organic phase over sodium sulphate, concentrate and distil to obtain 58 g of the title compound with a BP of 93° at 0.1 mm Hg.

Workup

  1. extractionrender alkaline with caustic soda solution and extract with dichlormethane
  2. dry with materialDry the organic phase over sodium sulphate
  3. concentrationconcentrate
  4. customdistil

Sources & evidence

ORD record
ord-21323675bc27472ba43cbb65f44ca2dc
Source dataset
uspto-grants-1980_09
Patent number
US04221788

Linked notes

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