Hydrochloric Acid → HCID 68615393, compound

HRID 859223Notes

Reaction equation

HRID 859223 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)=[CH:16][CH:15]=2)[CH2:9]1)(C)(C)C.[ClH:30]>O1CCCC1>[ClH:30].[NH2:7][CH:8]1[CH2:9][N:10]([C:14]2[CH:15]=[CH:16][C:17](/[CH:20]=[CH:21]/[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)=[CH:18][CH:19]=2)[C:11](=[O:13])[CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68615579HCID 68615579, compound

Product 1

HCID 68615393HCID 68615393, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 104 mg (0.26 mmol) of (RS)-(E)- (1-{4-[2-(3-fluoro-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidin-3-yl)-carbamic acid tert-butyl ester in 2.5 ml of tetrahydrofurane is treated with 192 mg of hydrochloric acid (37%). The mixture is warmed to 45° C. for 2 hours, then left under stirring for 18 hours at RT. The product precipitates partially from the reaction mixture which is evaporated to yield the crude hydrochloride. This is recrystallised from ether to give 74 mg (85% of theory) of (RS)-(E)-4-amino-1-{4-[2-(3-fluoro-phenyl)-vinyl]-phenyl}-pyrrolidin-2-one hydrochloride as a white solid; MS: m/e=297 (M+H)+.

Workup

  1. waitleft
  2. customThe product precipitates partially from the reaction mixture which
  3. customis evaporated
  4. customto yield the crude hydrochloride
  5. customThis is recrystallised from ether

Sources & evidence

ORD record
ord-8822448b66204fb7863e82f0a3f3fae2
Source dataset
uspto-grants-2006_12
Patent number
US07151111B2

Reaction notes

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