Thionyl Chloride → (3-Chloro-propylamino)-(4-fluoro-phenyl)-acetic acid methyl ester

HRID 1644815Notes

Reaction equation

HRID 1644815 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7](=[O:21])[CH:8]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[NH:9][CH2:10][CH2:11][CH2:12]O>C(Cl)(Cl)Cl>[CH3:5][O:6][C:7](=[O:21])[CH:8]([NH:9][CH2:10][CH2:11][CH2:12][Cl:3])[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66773976(4-Fluoro-phenyl)-(3-hydroxy-propylamino)-acetic acid methyl ester

Product 1

HCID 66774470(3-Chloro-propylamino)-(4-fluoro-phenyl)-acetic acid methyl esterYield 93.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of thionyl chloride (8.79 g) in chloroform (20 mL) was added (4-fluoro-phenyl)-(3-hydroxy-propylamino)-acetic acid methyl ester (14.85 g, dissolved in 60 mL of chloroform) dropwise via syringe. The reaction mixture was then stirred for 1.5 hours at 50° C. and the volatiles were subsequently removed in vacuo to give a solid residue which was triturated with diethyl ether (30 mL) to give the desired HCl salt of (3-chloro-propylamino)-(4-fluoro-phenyl)-acetic acid methyl ester (14.88 g, MS (ES+): 260.1 (MH+)) as an off-white solid.

Workup

  1. customthe volatiles were subsequently removed in vacuo
  2. customto give a solid residue which
  3. customwas triturated with diethyl ether (30 mL)

Sources & evidence

ORD record
ord-c96a7e3db7ff4ef393e2c4cef7b44a97
Source dataset
uspto-grants-2012_02
Patent number
US08124636B2

Reaction notes

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