Potassium Carbonate → 3-(4-benzylpiperidin-1-yl)-N-(2-tert-butoxybenzyl)-N-(pyridin-2-ylmethyl)propan-1-amine

HRID 403128ノート

反応式

HRID 403128 の反応式
[C:1]([O:5][C:6]1[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=1[CH2:8][N:9]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)([CH3:4])([CH3:3])[CH3:2].[CH2:36](C1CCNCC1)C1C=CC=CC=1.C(OC1C=CC=CC=1CN(CC1C=CC=CN=1)CCCCl)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:19]([CH:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][N:9]([CH2:8][C:7]2[CH:32]=[CH:33][CH:34]=[CH:35][C:6]=2[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:14][CH2:15]1)[C:24]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:36]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 67128530N-(2-tert-butoxybenzyl)-3-chloro-N-(pyridin-2-ylmethyl)propan-1-amineHCID 70896369N-(2-tert-butoxybenzyl)-3-(4-phenylpiperidin-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amine

生成物 1

HCID 708963903-(4-benzylpiperidin-1-yl)-N-(2-tert-butoxybenzyl)-N-(pyridin-2-ylmethyl)propan-1-amine収率 64%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The same procedure as described for compound 20 was applied to 4-benzyl piperidin (0.30 g, 1.73 mmol), compound 19 (0.4 g, 1.15 mmol), KI (0.57 g, 3.45 mmol) and K2CO3 (0.79 g, 5.75 mmol). The residue was redissolved in CH2Cl2 and chromatographed on a silica-gel column with the following eluents: 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as yellow oil (64% yield). 1H NMR (CDCl3) δ 8.453 (dd, 1H, Ar), 7.576 (ddd, 1H, Ar), 7.516 (m, 2H, Ar), 7.224 (m, 2H, Ar), 7.135 (m, 1H, Ar), 7.075 (m, 4H, Ar), 6.982 (m, 2H, Ar), 3.730 (s, 2H, —CH2—), 3.655 (s, 2H, —CH2—), 2.864 (d, 2H, —CH2—), 2.482 (t, 4H, —CH2—CH2—), 2.324 (t, 2H, —CH2—), 1.888 (t, 2H, —CH2—), 1.728 (p, 2H, —CH2—), 1.586 (d, 2H, —CH2—), 1.502 (m, 1H, —CH—), 1.324 (s, 9H, —C(CH3)3), 1.288 (overlapped m, 2H, —CH2—). Mass Spec.=486.35 (M+H)+.

後処理

  1. customchromatographed on a silica-gel column with the following eluents

出典と根拠

ORDレコード
ord-d5602439f1e342639c0375fe25d43cc2
出典データセット
uspto-grants-2014_06
特許番号
US08747810B2

反応ノート

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