Triethylamine → HCID 16222599, compound

HRID 2250468Notes

Reaction equation

HRID 2250468 reaction equation
ClC1C=CSC=1C([N:9]([C:11]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[NH2:10])=O.[Cl:19][C:20]1[CH:24]=[CH:23][S:22][C:21]=1[C:25](NN)=O.CCN(CC)CC.N1(C(Cl)=O)CCCCC1>O.C1COCC1>[Cl:19][C:20]1[CH:24]=[CH:23][S:22][C:21]=1[C:25]1[O:12][C:11]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)=[N:9][N:10]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2420851-Piperidinecarbonyl chlorideHCID 23570764HCID 23570764, compoundHCID 69104970HCID 69104970, compound

Product 1

HCID 16222599HCID 16222599, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Piperidine-1-carboxylic acid N-(3-chlorothiophene-2-carbonyl)-hydrazide. A yellow solution of 3-chlorothiophene-2-carboxylic acid hydrazide (0.150 g, 0.852 mmol), THF (1.7 mL) and Et3N (0.12 mL, 0.852 mmol) was cooled to 0° C. and 1-piperidinecarbonyl chloride (0.106 mL, 0.852 mmol) was added dropwise. The yellow solution was equilibrated to room temperature and stirred for 18 h The reaction solution was diluted with water (20 mL) and then extracted with ethyl acetate (30 mL). The organic layer was washed with water (15 mL), brine (10 mL), dried over MgSO4, and then concentrated to yield 0.210 g (86%) of the title compound as a white solid. 1H NMR (CDCl3): 9.29 (d, 1H, J=5.2 Hz), 7.51-7.48 (m, 2H), 7.00 (d, 1H, J=5.2 Hz), 3.45-3.43 (m, 4H), 1.64-1.60 (m, 6H).

Workup

  1. customwas equilibrated to room temperature
  2. extractionextracted with ethyl acetate (30 mL)
  3. washThe organic layer was washed with water (15 mL), brine (10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c74b54f66a945a183b0486f0fa7acdf
Source dataset
uspto-grants-2008_01
Patent number
US07317029B2

Reaction notes

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