Sodium cyanoborohydride → tert-Butyl 2-(4-(dimethylamino)-4-phenylpiperidin-1-yl)ethyl(methyl)carbamate

HRID 2387927Notes

Reaction equation

[CH3:1][N:2]([CH3:15])[C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH3:16][N:17]([CH2:25][CH:26]=O)[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].C([BH3-])#N.[Na+]>CO.C(O)(=O)C.CO.C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:15])[C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:5][N:6]([CH2:26][CH2:25][N:17]([CH3:16])[C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:7][CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

7 g (1 equiv.) of N,N-dimethyl-4-phenylpiperidine-4-amine were added in portions to a solution of 6.5 g (1.5 equiv.) of tert-butyl methyl(2-oxoethyl)carbamate in 60 ml of methanol. The reaction mixture was cooled to 0° C., 3.97 g (2.5 equiv.) of sodium cyanoborohydride were added in portions, and stirring was then carried out for 10 minutes at room temperature. The resulting reaction mixture was adjusted to a pH of ˜5 by means of acetic acid and was stirred for 12 hours at room temperature. The progress of the reaction was monitored by means of thin-layer chromatography (20% MeOH/CHCl3). Because the reaction was not yet complete, 1.5 g of sodium cyanoborohydride and acetic acid were added and the reaction mixture was stirred for a further 35-40 minutes.

Workup

customThe resulting reaction mixture
stirringwas stirred for 12 hours at room temperature
stirringthe reaction mixture was stirred for a further 35-40 minutes

Sources & evidence

ORD record: ord-a1385dd86a9e45579fbc1c13850297d5
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08269000B2

Reaction notes

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