N-Methylbenzylamine → Benzyl-cyclohexylmethyl-methyl-amine

HRID 1714111Notes

Reaction equation

HRID 1714111 reaction equation
S(=O)(O)O.[CH:5]1([CH:11]=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.CCN(CC)CC.[CH3:20][NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.CCOC(C)=O>[CH2:11]([N:21]([CH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[CH3:20])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 7669N-MethylbenzylamineHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86612818Cyclohexanecarboxaldehyde bisulfite

Product 1

HCID 12869919Benzyl-cyclohexylmethyl-methyl-amine

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of cyclohexanecarboxaldehyde bisulfite adduct (5.0 mmol) and Et3N (5.5 mmol) in dichloroethane (20 mL) was stirred at room temperature for 15 min. The suspension was treated with N-methylbenzylamine (5.5 mmol) and was stirred for 45 min. NaBH(OAc)3 (7.0 mmol) was added portion-wise over approximately 30 min. After 16 h, the reaction mixture was diluted with EtOAc (80 mL), and was washed with 1 N NaOH (25 mL) followed by brine (25 mL). The organic layer was dried (MgSO4) and concentrated to yield benzyl-cyclohexylmethyl-methyl-amine as an oil. The crude material was purified by the General Purification Method as described above.

Workup

  1. stirringwas stirred for 45 min
  2. waitAfter 16 h
  3. washwas washed with 1 N NaOH (25 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c48a5190a8f545a4a5f284472e82033f
Source dataset
uspto-grants-2010_09
Patent number
US07795426B2

Reaction notes

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