Acetic Acid → [(4,4-Dimethyl cyclohexyl)methyl](phenylmethyl)amine

HRID 471801Notes

Reaction equation

HRID 471801 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH:5]([CH:8]=O)[CH2:4][CH2:3]1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH:5]([CH2:8][NH:18][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 222352954,4-Dimethylcyclohexane-1-carbaldehyde

Product 1

HCID 59474634[(4,4-Dimethyl cyclohexyl)methyl](phenylmethyl)amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4,4-dimethylcyclohexanecarbaldehyde (6.6 g, 0.047 mol), benzylamine (5.0 g, 0.047 mol) and acetic acid (1 mL) in methanol (60 mL) was stirred for 30 min at room temperature. Sodium triacetoxyborohydride (10.0 g, 0.047 mol) was added in one portion and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated in vacuo and partitioned between dichloromethane and water. The organic phase was washed with brine, silica gel was added and the mixture was concentrated in vacuo. The residue was purified by flash chromatography (CH2Cl2/MeOH), affording [(4,4-dimethyl cyclohexyl)methyl](phenylmethyl)amine as a white solid. (M+H) 232, 1.76 min. (LC/MS method B).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between dichloromethane and water
  3. washThe organic phase was washed with brine, silica gel
  4. additionwas added
  5. concentrationthe mixture was concentrated in vacuo
  6. customThe residue was purified by flash chromatography (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-f80a181f38b6481fa79808713d471551
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Reaction notes

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