Formaldehyde → 1-Benzyl-4-(dimethylamino)piperidine

HRID 482295Notes

Reaction equation

HRID 482295 reaction equation
N[CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[CH2:15]=O.[BH3-][C:18]#[N:19].[Na+]>O>[CH3:15][N:19]([CH3:18])[CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4158521-Benzyl-4-piperidylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 4160661-Benzyl-4-(dimethylamino)piperidineYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-amino-1-benzylpiperidine (1.47 g, 7.7 mmol) in CF3 CH2OH (14 ml) were added molecular sieve 4 Å (5), and paraformaldehyde (0.51 g, 17 mmol). After stirring at RT for 1 h, NaCNBH3 (2.5 g, 39.8 mmol) was added and stirred for 16 h at RT. The reaction was stopped by addition of H2O and the product was extracted with (4:1) (Et2O:CH2Cl2). Organic fractions were combined and washed with brine (2×), dried over MgSO4, filtered and concentrated to give a crude material which was purified by silica flash chromatography to afford 4-dimethylamino-1-benzylpiperidine (80% yield). FAB Mass [M+1]+35Cl 219.

Workup

  1. stirringstirred for 16 h at RT
  2. extractionthe product was extracted with (4:1) (Et2O:CH2Cl2)
  3. washwashed with brine (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude material which
  8. customwas purified by silica flash chromatography

Sources & evidence

ORD record
ord-791b78be97ce41668cf52ff92dd661ff
Source dataset
uspto-grants-1998_08
Patent number
US05795894

Reaction notes

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