Formaldehyde → 1-(4-Chlorobenzyl)-4-{(methylamino)methyl}piperidine

HRID 2187858Notes

Reaction equation

C=O.[Cl:3][C:4]1[CH:18]=[CH:17][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH2:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.[BH3-][C:20]#N.[Na+]>CC(O)=O.CO>[Cl:3][C:4]1[CH:18]=[CH:17][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][CH3:20])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Formaldehyde (108 mg, 1.33 mmol, 37% wt solution in H2O) was added to a solution of 1-(4-chlorobenzyl)-4-(aminomethyl)piperidine (318 mg, 1.33 mmol) and NaBH3CN (668 mg) in 10% CH3COOH/CH3OH (3 mL). The reaction mixture was stirred at 25° C. for 1 h. The reaction mixture was loaded on DOWEX™ 50W×2 column (10 mL) and washed with CH3OH (100 mL). Product was eluted off using 2 N NH3 in CH3OH (100 mL) and concentrated to afford 173 mg of crude 1-(4-chlorobenzyl)-4-{(methylamino)methyl}piperidine as a colorless oil used without purification.

Workup

washwashed with CH3OH (100 mL)
washProduct was eluted off
concentrationconcentrated

Sources & evidence

ORD record: ord-8b8ebff0922f4dfe88a714c3b88a9136
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410566B1

Reaction notes

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