Triethylamine → HCID 18364767, compound

HRID 380473Notes

Reaction equation

HRID 380473 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]3[CH:19]([C:20]4[CH:24]=[CH:23][S:22][CH:21]=4)[CH2:18][NH:17][CH2:16]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:32][C:33]1[N:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36]>C(Cl)Cl>[Cl:32][C:33]1[C:34]([C:35]([N:17]2[CH2:18][CH:19]([C:20]3[CH:24]=[CH:23][S:22][CH:21]=3)[CH:15]([CH2:14][N:11]3[CH2:10][CH2:9][CH:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:13][CH2:12]3)[CH2:16]2)=[O:36])=[CH:38][CH:39]=[CH:40][N:41]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27745412-Chloronicotinoyl chlorideHCID 18364725HCID 18364725, compound

Product 1

HCID 18364767HCID 18364767, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.105 g (0.3 mmol) of 3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine, 0.082 mL (0.6 mmol) of triethylamine and 0.054 g (0.3 mmol) of 2-chloronicotinoyl chloride (Aldrich) in 6 mL of CH2Cl2 was stirred at rt for 4 h. The reaction mixture was concentrated and the residue was purified by chomatography (silica, hexanes: acetone=3:1) to afford 0.12 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chomatography (silica, hexanes: acetone=3:1)

Sources & evidence

ORD record
ord-b9efc2ac0718488f8d1f9ae683918d2b
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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