3-Cyanomethyl-4-chloro-5-benzyloxyindole → 3-(2-Aminoethyl)-4-chloro-5-benzyloxyindole

HRID 1898986Notes

Reaction equation

HRID 1898986 reaction equation
[C:1]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]=2[Cl:13])[NH:6][CH:5]=1)#[N:2]>N.[Ni]>[NH2:2][CH2:1][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:11]=2[Cl:13])[NH:6][CH:5]=1

Participants

4

Reactant 1

HCID 233730833-Cyanomethyl-4-chloro-5-benzyloxyindole

Product 1

HCID 233730503-(2-Aminoethyl)-4-chloro-5-benzyloxyindoleYield 103.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

A solution of 3-cyanomethyl-4-chloro-5-benzyloxyindole (1.00 g, 3.37 mmol) in methanolic ammonia (30 ml) was hydrogenated over Raney nickel for 21/2 hours at room temperature, at 30 p.s.i. pressure. After filtering off the catalyst, the filtrate was evaporated to give 3-(2-aminoethyl)-4-chloro-5-benzyloxyindole as an oil (1.05 g, 100%). Part of this product (170 mg, 0.57 mmol) was treated with excess ethereal HCl, and the mixture was evaporated to dryness to leave a pink solid, which was recrystallised from ethanol/ether to give 3-(2-amino-ethyl)-4-chloro-5-benzyloxyindole hydrochloride (108 mg) m.p. 224°-5° C.

Workup

  1. custom2 hours
  2. customat room temperature
  3. filtrationAfter filtering off the catalyst
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-9cd49f34dba34d66baf940a30bafe8ca
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

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