Hydrochloric Acid → HCID 66705875, compound

HRID 2276372Notes

Reaction equation

HRID 2276372 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)[CH2:9]1)=O)(C)(C)C.Cl>C1COCC1.O1CCOCC1>[ClH:27].[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([CH:10]3[CH2:11][CH2:12][NH:8][CH2:9]3)=[CH:14][CH:15]=2)=[O:28])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66705849HCID 66705849, compound

Product 1

HCID 66705875HCID 66705875, compoundYield 166.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of (RS)-3-[4-(4-chloro-benzoylamino)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (2.36 g) in THF (30 ml) was added dropwise a solution of hydrogen chloride in dioxane (22 ml, 4 M solution) and the mixture was heated at 60° C. overnight. The mixture was then cooled to 0° C. and the ensuing crystals were collected by filtration, washing with diethyl ether, and then dried in vacuo at 60° C. to afford (RS)-4-chloro-N-(4-pyrrolidin-3-yl-phenyl)-benzamide hydrochloride (1.65 g, 83%) as a white crystalline solid. MS (ISP): 303.2 ([{37Cl}M+H]+), 301.3 ([{35Cl}M+H]+).

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. filtrationthe ensuing crystals were collected by filtration
  3. washwashing with diethyl ether
  4. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-40f0b8b0e1fe48648b76388849a8d150
Source dataset
uspto-grants-2015_09
Patent number
US09132136B2

Reaction notes

Loading…