4-Benzylpiperidine → N-[3-(4-benzylpiperidin-1-yl)-1-phenylpropyl]benzenesulfonamide

HRID 860172ノート

反応式

HRID 860172 の反応式
[CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[CH:15][CH2:16][CH:17]([NH:24][S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([BH3-])#N.[Na+]>CO>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH:17]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 317384-BenzylpiperidineHCID 5003444Sodium cyanoborohydrideHCID 86590616N-(3-Oxo-1-phenylpropyl)benzenesulfonamide

生成物 1

HCID 10138689N-[3-(4-benzylpiperidin-1-yl)-1-phenylpropyl]benzenesulfonamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-Benzylpiperidine (54 μL, 0.30 mmol) was added to a stirred solution of N-(3-oxo-1-phenylpropyl)benzenesulfonamide (83 mg, 0.28 mmol) (Example 3 Step 4) in MeOH (1.0 mL) under N2 and sodium cyanoborohydride (40 mg, 0.62 mmol) added. After 4 h the reaction was quenched with water, applied to an SCX-2 cartridge and washed with MeOH and then 2 M NH3 in MeOH solution. The desired fractions were concentrated under reduced pressure and further purified by reversed phase prep-HPLC system to give the title compound as a residue (10 mg, 7%), after isolating the free base. 1H NMR (400 MHz, CDCl3) δ 1.3–2.0 (9H, m), 2.25–2.40 (2H, m), 2.59 (2H, d, J 6.9 Hz), 2.91 (2H, t, J 9.4 Hz), 4.50–4.54 (1H, m), 7.08–7.22 (8H,m), 7.27–7.36 (4H, m), 7.41–7.46 (1H, m), 7.64–7.69 (2H,m). MS (ES+) C27H32N2O2S requires: 448, found: 449 (M+H+)

後処理

  1. customAfter 4 h the reaction was quenched with water
  2. washwashed with MeOH
  3. concentrationThe desired fractions were concentrated under reduced pressure
  4. customfurther purified by reversed phase prep-HPLC system

出典と根拠

ORDレコード
ord-0311cbf8d26348bbaaac9285bfe8cd71
出典データセット
uspto-grants-2006_12
特許番号
US07153868B2

反応ノート

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