Tetrahydrofuran → Tert-butyl 4-{3-[(6-bromohexanoyl)amino]phenyl}-1-piperidine carboxylate

HRID 1452650ノート

反応式

HRID 1452650 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28].C(N(CC)CC)C.C1COCC1>C(Cl)(Cl)Cl>[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([NH:20][C:16]1[CH:15]=[C:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[CH:19]=[CH:18][CH:17]=1)=[O:28]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 898486-Bromohexanoyl chlorideHCID 22049268tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylate

生成物 1

HCID 57526937Tert-butyl 4-{3-[(6-bromohexanoyl)amino]phenyl}-1-piperidine carboxylate収率 101.6%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A 25-mL RB-flask, charged with tert-butyl-4-[3-(amino)phenyl]-1-piperidinecarboxylate (2.00 mmol, 0.553 g), 6-bromohexanoyl chloride (0.427 g, 2.00 mmol, 1.0 eq.), triethylamine (0.404 g, 4.00 mmol) and THF (8.00 mL) was stirred at room temperature for 4 h. The reaction mixture was diluted with chloroform (50 mL) and washed with water (100 mL), brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography (silica gel, hexanes/EtOAc 10:1) to yield the desired product (0.921 g, 95.8%). 1H NMR (400 MHz, CDCl3) δ 7.47 (s, 1H), 7.28-7.22 (m, 2H), 7.11 (s, 1H), 6.5 (d, 1H, J=7.0 Hz), 3.45-3.39 (m, 2H), 2.85-2.70 (m, 2H), 2.68-2.58 (m, 1H), 2.37 (t, 2H, J=7.4 Hz), 1.96-1.71 (m, 7H), 1.68-1.50 (m, 5H), 1.48 (s, 9H); ESMS m/e: 355.4, 476.6.

後処理

  1. washwashed with water (100 mL), brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography (silica gel, hexanes/EtOAc 10:1)

出典と根拠

ORDレコード
ord-b3bc0ef9ae9949bc8ca099c773ff4e79
出典データセット
uspto-grants-2009_01
特許番号
US07473698B2

反応ノート

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