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

HRID 2108308Notes

Reaction equation

HRID 2108308 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 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.

Workup

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

Sources & evidence

ORD record
ord-88e5ef5a14e44e469a8964bd17a3b65b
Source dataset
uspto-grants-2009_04
Patent number
US07514225B2

Reaction notes

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