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

HRID 1452650노트

반응식

HRID 1452650 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b3bc0ef9ae9949bc8ca099c773ff4e79
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473698B2

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