Water → N-[1-(3-Chloropropyl)piperidin-4-yl]-4-fluorobenzamide

HRID 1531828Notes

Reaction equation

HRID 1531828 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][Cl:27].O>CN(C)C=O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:24][CH2:25][CH2:26][Cl:27])[CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 47782264-fluoro-N-(piperidin-4-yl)benzamide

Product 1

HCID 20574365N-[1-(3-Chloropropyl)piperidin-4-yl]-4-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 10.65 g of 4-(4-fluorobenzamido)piperidine (preparation 2) and potassium carbonate (9.93 g) in 160 ml of dry dimethylformamide was cooled to 0° C. and a solution of 1-bromo-3-chloropropane (5.68 ml) in 5.68 ml of dry dimethylformamide added dropwise thereto. After 3 hours at room temperature the reaction mixture was poured into 1600 ml of water and stirred for one hour. The solid which precipitated was recovered by filtration (7.1 g).

Workup

  1. customThe solid which precipitated
  2. filtrationwas recovered by filtration (7.1 g)

Sources & evidence

ORD record
ord-63f8641b1b7c4f16a3efd10410e403e1
Source dataset
uspto-grants-2001_03
Patent number
US06200989B1

Reaction notes

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