Triethylamine → 1-(3,4-Difluorobenzoyl)-3-(RS)-(4-phenylpiperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine

HRID 380469Notes

Reaction equation

HRID 380469 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH:14]3[CH:18]([C:19]4[CH:23]=[CH:22][S:21][CH:20]=4)[CH2:17][NH:16][CH2:15]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[F:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[F:41])[C:35](Cl)=[O:36]>C(Cl)Cl>[F:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[F:41])[C:35]([N:16]1[CH2:17][CH:18]([C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)[CH:14]([CH2:13][N:10]2[CH2:9][CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12][CH2:11]2)[CH2:15]1)=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27245193,4-Difluorobenzoyl chlorideHCID 206944833-(SR)-(4-phenyl piperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine

Product 1

HCID 183648201-(3,4-Difluorobenzoyl)-3-(RS)-(4-phenylpiperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidineYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.023 g (0.071 mmol) of 3-(SR)-(4-phenylpiperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine and 0.079 mL of Et3N in 2 mL of CH2Cl2 was added 0.059 g (0.28 mmol) of 3,4-difluorobenzoyl chloride and the reaction mixture was stilled for 0.5 h. The reaction mixture was partitioned between CH2Cl2 and sat'd NaHCO3 solution. The organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chomatography (silica, acetone: hexanes, 1:3) to give 0.026 g of the title compound. 1H NMR (CDCl3) δ7.17-7.49 (m, 9H), 7.13 and 7.08 (s, 1H), 7.04 and 6.99 (d, 1H, J=4.6 Hz),4.08-4.15 (m, 2H); Mass Spectrum (CI) m/e=482 (M+1).

Workup

  1. customThe reaction mixture was partitioned between CH2Cl2 and sat'd NaHCO3 solution
  2. dry with materialThe organic fraction was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chomatography (silica, acetone: hexanes, 1:3)

Sources & evidence

ORD record
ord-79c3f57b767a4452be5485cb6aa68644
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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