Ammonium Hydroxide → HCID 53725336, compound

HRID 839307Notes

Reaction equation

HRID 839307 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([C:7]([CH2:15][CH3:16])([OH:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#N.[OH-].[NH4+].[NH2:21][CH2:22]C1C=CC(C(CC)(O)C2C=CC=CC=2)=CC=1>[Ni].C(O)C>[NH2:21][CH2:22][CH2:1][C:3]1[CH:18]=[CH:17][C:6]([C:7]([CH2:15][CH3:16])([OH:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 20324262HCID 20324262, compoundHCID 20324277HCID 20324277, compound

Product 1

HCID 53725336HCID 53725336, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

24 g. of 4-cyano-α-ethyl-benzhydrol are dissolved in 192 ml. of ethanol, and 48 ml. of a 25% aqueous ammonium hydroxide solution and 9.6 g. of Raney-nickel are added. The reaction mixture is hydrogenated at 50° C. After the uptake of the theoretical amount of hydrogen the catalyst is filtered off, and the clear filtrate is evaporated to dryness under reduced pressure. The solid residue is recrystallized from a mixture of n-heptane and benzene to yield 17 g. of 4-aminomethyl-α-ethyl-benzhydrol melting at 97.5°-98.5° C.

Workup

  1. customis hydrogenated at 50° C
  2. filtrationAfter the uptake of the theoretical amount of hydrogen the catalyst is filtered off
  3. customthe clear filtrate is evaporated to dryness under reduced pressure
  4. customThe solid residue is recrystallized from a mixture of n-heptane and benzene
  5. customto yield 17 g

Sources & evidence

ORD record
ord-293f02b77ee3453998434e5b949b8e70
Source dataset
uspto-grants-1978_06
Patent number
US04094908

Reaction notes

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