Propylamine → 3-(4-Fluorophenyl)-N-propylpropan-1-amine

HRID 1592351Notes

Reaction equation

HRID 1592351 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]=O)=[CH:4][CH:3]=1.[CH2:12]([NH2:15])[CH2:13][CH3:14].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH:15][CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 101977823-(4-Fluorophenyl)propanal

Product 1

HCID 469064523-(4-Fluorophenyl)-N-propylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the crude 3-(4-fluorophenyl)propanal and propylamine (3.0 g, 51 mmol) in CH2Cl2 and was treated with NaBH(OAc)3 and stirred at room temperature overnight. The reaction was quenched with 1 N NaOH, and washed successively with water and brine. The solvent was evaporated under vacuum to give 4.3 g of 3-(4-fluorophenyl)-N-propylpropan-1-amine.

Workup

  1. customThe reaction was quenched with 1 N NaOH
  2. washwashed successively with water and brine
  3. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-290aa98cebed4ffe9d3b01e063a88153
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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