Sodium Hydroxide → (S)-1-(4-bromophenyl)propan-1-amine

HRID 2037444Notes

Reaction equation

HRID 2037444 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:11]C(=O)C(F)(F)F)[CH2:9][CH3:10])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH2:11])[CH2:9][CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58109241(S)-N-(1-(4-bromophenyl)propyl)-2,2,2-trifluoroacetamide

Product 1

HCID 7127717(S)-1-(4-bromophenyl)propan-1-amineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)—N-(1-(4-bromophenyl)propyl)-2,2,2-trifluoroacetamide (45.24 g, 0.1464 mol) in methanol (317 mL) was added a solution of NaOH (188 mL, 13%) at 0° C. The mixture was stirred for 2 h. The mixture was concentrated and extracted with methylene chloride. The solvent was removed to give (S)-1-(4-bromophenyl)propan-1-amine (29.65 g, 95%). 1H NMR (CDCl3): 084 (t, 3H), 1.63 (m, 2H), 3.79 (m, 1H), 7.19 (m, 2H), 7.45 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with methylene chloride
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-4bba1ccc36014b4682989269c0e45f7c
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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