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

HRID 6689

Reaction equation

HRID 6689 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

2-Thiophenecarbonylchloride (2.04 g, 1.49 mL) was added to a solution of tertbutyl-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.

Workup

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

Sources & evidence

ORD record
ord-e54e6113600045fa9609df769f8eb552
Source dataset
uspto-grants-2006_08
Patent number
US07084141B2

Linked notes

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