Triethylamine → HCID 19097478, compound

HRID 486078Notes

Reaction equation

HRID 486078 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH3:8])[C:4]([CH3:12])([CH2:9][CH2:10][NH2:11])[CH:3]1[CH3:13].C(N(CC)CC)C.[S:21]1[CH:25]=[CH:24][C:23]([C:26](Cl)=[O:27])=[CH:22]1>C(Cl)Cl.CCOCC>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH3:8])[C:4]([CH2:9][CH2:10][NH:11][C:26]([C:23]2[CH:24]=[CH:25][S:21][CH:22]=2)=[O:27])([CH3:12])[CH:3]1[CH3:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27763773-Thenoyl chlorideHCID 19097467HCID 19097467, compound

Product 1

HCID 19097478HCID 19097478, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1,2,3,4-tetramethyl-3-piperidineethanamine (2.9 g, I6 mmol), triethylamine (10 mL) and methylene chloride (25 mL) was cooled to 0° C. and 3-thiophenecarboxylic acid chloride (2.3 g, 16 mmol) in methylene chloride (15 mL) was added. The reaction mixture was warmed to room temperature and stirred for 16 hours. The reaction mixture was diluted with ether (200 mL) and washed with saturated sodium bicarbonate (2×50 mL), water (50 mL), then brine (50 mL). The organic layer was separated, dried over Na2SO4 and treated with charcoal. The solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with ether (100%), then 2% diisopropylamine/ether, followed by 5% isopropylamine/ether to afford 2.9 g (62%) of N-[2-(1,2,3,4-tetramethyl-3-piperidinyl)-ethyl]-3-thiophenecarboxamide as an oil. The product was dissolved in ethanol (7 mL), cooled to 0° C., treated with 3.2N ethanolic HCl and diluted with ether to afford 3.1 g of the hydrochloride salt as a yellow solid. The salt was recrystallized from ethanol/ether and had a melting point of 228°-229° C.

Workup

  1. washwashed with saturated sodium bicarbonate (2×50 mL), water (50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. additiontreated with charcoal
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by column chromatography on silica eluting with ether (100%)

Sources & evidence

ORD record
ord-1a26ac9e7ebf4f2e954e783e74a5c9d8
Source dataset
uspto-grants-1994_03
Patent number
US05290796

Reaction notes

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