Hydrochloric Acid → (S)-1-(3-(cyclopentyloxy)-4-methoxyphenyl)-3-(pyrrolidin-1-ylmethyl)piperazine, dihydrochloride

HRID 1423104Notes

Reaction equation

HRID 1423104 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:10][C@@H:9]1[CH2:28][N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)=O)(C)(C)C.[ClH:34]>O1CCOCC1>[ClH:34].[ClH:34].[CH:23]1([O:22][C:16]2[CH:15]=[C:14]([N:11]3[CH2:12][CH2:13][NH:8][C@@H:9]([CH2:28][N:29]4[CH2:30][CH2:31][CH2:32][CH2:33]4)[CH2:10]3)[CH:19]=[CH:18][C:17]=2[O:20][CH3:21])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66826381(S)-4-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-pyrrolidin-1-ylmethyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 131732229(S)-1-(3-(cyclopentyloxy)-4-methoxyphenyl)-3-(pyrrolidin-1-ylmethyl)piperazine, dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The intermediate (S)-4-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-pyrrolidin-1-ylmethyl-piperazine-1-carboxylic acid tert-butyl ester (300 mg, 0.65 mmol) was then dissolved in 1,4-dioxane (2 mL) and treated with a 4 N solution of hydrogen chloride in 1,4-dioxane (4 mL) and stirred for 3 h. The reaction was then evaporated to afford the title compound as a colorless solid. (280 mg, 99%). LC/MS (Method B) 1.05 min, [M+1]+ 360.

Workup

  1. customThe reaction was then evaporated

Sources & evidence

ORD record
ord-5d409b02c70745c69980d7ca86857acb
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

Loading…