Triethylamine → 1-Propanone, 1-[4-(4-chloro-2-pyridinyl)-1-piperazinyl]-2,2-dimethyl-

HRID 1993646Notes

Reaction equation

HRID 1993646 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:4]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:10][CH2:11][N:12]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:13][CH2:14]2)[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 685418771255099-59-2

Product 1

HCID 685369901-Propanone, 1-[4-(4-chloro-2-pyridinyl)-1-piperazinyl]-2,2-dimethyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir 1-(4-chloro-pyridin-2-yl)-piperazine hydrochloride (2.2 mmol, 0.4 g), triethylamine (7.6 mmol, 1.1 mL) in 13 mL of CH2Cl2 and pivaloyl chloride (2.2 mmol, 0.3 mL) overnight at room temperature. Add CH2Cl2 and wash with saturated aq. sodium chloride and water. Dry over sodium sulfate, filter, and concentrate under reduced pressure to give 1-[4-(4-chloro-pyridin-2-yl)-piperazin-1-yl]-2,2-dimethyl-propan-1-one. MS(ES): m/z=282 [M+H].

Workup

  1. washAdd CH2Cl2 and wash with saturated aq. sodium chloride and water
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-7fd8816ee2014e85aea887fd2284e6d6
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

Loading…