Amino-alpha-ethyl-benzhydrol → 3-Amino-alpha-ethyl-benzhydrol

HRID 839308Notes

Reaction equation

HRID 839308 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1Cl)[C:5]([CH2:13][CH3:14])([OH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.NC1C=CC=CC=1C(CC)(O)C1C=CC=CC=1>CO.[OH-].[K+]>[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([CH2:13][CH3:14])([OH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 2803285Amino-alpha-ethyl-benzhydrolHCID 20324253HCID 20324253, compound

Product 1

HCID 203242593-Amino-alpha-ethyl-benzhydrol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

2.6 g. of 3-amino-4-chloro-α-ethyl-benzhydrol are dissolved in methanol containing 3.9 g of potassium hydroxide. 8.7 g. of an 5% palladium-on-calcium carbonate catalyst are added to the mixture, and the suspension is hydrogenated at room temperature under atmospheric pressure. After the uptake of the calculated amount of hydrogen the catalyst is filtered off and washed with 15 ml. of methanol. The filtrate and the wash are combined and concentrated to 40 ml. under reduced pressure. The product is precipitated from the concentrate with water. The solids are filtered off, washed until neutral, and dried until constant weight. The crude product is recrystallized from alcohol to yield 1.7 g. of 3 amino-α-ethyl-benzhydrol, melting at 92-93° C.

Workup

  1. customis hydrogenated at room temperature under atmospheric pressure
  2. filtrationAfter the uptake of the calculated amount of hydrogen the catalyst is filtered off
  3. washwashed with 15 ml
  4. concentrationconcentrated to 40 ml
  5. customThe product is precipitated from the
  6. concentrationconcentrate with water
  7. filtrationThe solids are filtered off
  8. washwashed until neutral, and
  9. customdried until constant weight
  10. customThe crude product is recrystallized from alcohol
  11. customto yield 1.7 g

Sources & evidence

ORD record
ord-aa9bd2ae660a4af89b8c740503bc79b0
Source dataset
uspto-grants-1978_06
Patent number
US04094908

Reaction notes

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