2-Thiophenecarbonyl chloride → Tert-butyl 4-(thiophene-2-carbonyl)piperazine-1-carboxylate

HRID 14356

反応式

HRID 14356 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

参加物

5

反応物 2

HCID 789282-Thiophenecarbonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

生成物 1

HCID 2796164Tert-butyl 4-(thiophene-2-carbonyl)piperazine-1-carboxylate収率 88.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

2-Thiophenecarbonylchloride (2.04 g, 1.49 mL) was added to a solution of tert-butyl-1-piperazinecarboxylate (2.5 g, 13.4 mmol) and DMAP (20 mg) in pyridine (15 mL) at 0° C. under N2 atmosphere and stirred at room temperature for overnight. The mixture was poured into ice water, the precipitate was filtered, washed several times with water, and dried to yield white solids (3.5 g, 88%). Mp 76° C. 1H NMR (DMSO-d6): δ 1.42 (s, 12H), 3.40 (m, 4H), 3.61 (m, 4H), 7.12 (m, 1H), 7.43 (d, J=4.1 Hz, 1H), 7.77 (d, J=4.8 Hz, 1H). EIMS m/z 297 (M+1), 319 (M+23). Anal. (C14H20N2O3S) C, H, N.

後処理

  1. filtrationthe precipitate was filtered
  2. washwashed several times with water
  3. customdried

出典と根拠

ORDレコード
ord-2f59057de17345809ee82ef0e8995252
出典データセット
uspto-grants-2010_06
特許番号
US07732146B2

関連ノート

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