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

HRID 2387927
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HRID 2387927 반응식
[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
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참가 물질

7

반응물 3

HCID 5003444Sodium cyanoborohydride2회HCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateHCID 57831258N,N-dimethyl-4-phenylpiperidin-4-amine

생성물 1

HCID 68408263tert-Butyl 2-(4-(dimethylamino)-4-phenylpiperidin-1-yl)ethyl(methyl)carbamate

시약·촉매·용매 3

HCID 176Acetic Acid용매2회
HCID 887
Methanol
용매
HCID 21584188Chloroform methanol용매

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-a1385dd86a9e45579fbc1c13850297d5
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08269000B2

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