2-Thiophenecarbonyl chloride → HCID 21904808, compound

HRID 1270200Notes

Reaction equation

HRID 1270200 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].C([O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15])(C)(C)C>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:19]1[CH2:20][CH2:21][N:16]([C:14]([OH:15])=[O:13])[CH2:17][CH2:18]1)=[O:7]

Participants

5

Reactant 2

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

Product 1

HCID 21904808HCID 21904808, compoundYield 108.7%

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-e0a12e8ebaf7425192cbc8a60169b429
Source dataset
uspto-grants-2007_04
Patent number
US07202248B2

Reaction notes

Loading…