4-Methoxybenzaldehyde → Hept-6-enyl-(4-methoxy-benzyl)-amine

HRID 1803685Notes

Reaction equation

HRID 1803685 reaction equation
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]=O)=[CH:15][CH:16]=1.[BH4-].[Na+]>CCO>[CH2:1]([NH:8][CH2:17][C:14]1[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 12878168Hept-6-en-1-amine

Product 1

HCID 57956448Hept-6-enyl-(4-methoxy-benzyl)-amineYield 57.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of hept-6-enylamine (2.0 g, 13.4 mmol) and anisaldehyde (1.79 mL, 14.7 mmol) in EtOH (50 mL) was stirred at room temperature for 1 h. Then, NaBH4 (556 mg, 14.7 mmol) was added at 0° C. under nitrogen. The resulting solution was allowed to warm up to room temperature for 4 h. Then, the reaction mixture was partitioned between ice-cold water and CH2Cl2, washed with brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography (gradient AcOEt/CH2Cl2 0:1 to 2:8, then CH2Cl2/MeOH 9:1) to give 1.8 g (34%) of the title product 86 as a colorless oil: m/z=234 (M+H)+.

Workup

  1. customThen, the reaction mixture was partitioned between ice-cold water and CH2Cl2
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by chromatography (gradient AcOEt/CH2Cl2 0:1 to 2:8

Sources & evidence

ORD record
ord-e29c7e2e7bf24f82bc82bb321dbbb514
Source dataset
uspto-grants-2013_01
Patent number
US08349869B2

Reaction notes

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