1,4-Dioxane hydrochloride → 4-(2-(4-(Trifluoromethyl)benzyl)-2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole-8-carboxamido)piperidine dihydrochloride salt

HRID 1042535Notes

Reaction equation

HRID 1042535 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:38]=[CH:37][C:6]([CH2:7][N:8]2[CH2:36][CH2:35][C:11]3[NH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([NH:21][CH:22]5[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)=[O:20])=[CH:17][C:18]=4[C:10]=3[CH2:9]2)=[CH:5][CH:4]=1.[ClH:41].O1CCOCC1>>[ClH:41].[ClH:41].[F:40][C:2]([F:1])([F:39])[C:3]1[CH:38]=[CH:37][C:6]([CH2:7][N:8]2[CH2:36][CH2:35][C:11]3[NH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([NH:21][CH:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[O:20])=[CH:17][C:18]=4[C:10]=3[CH2:9]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 44177408tert-butyl 4-(2-(4-(trifluoromethyl)benzyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamido)piperidine-1-carboxylate

Product 1

HCID 665896624-(2-(4-(Trifluoromethyl)benzyl)-2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole-8-carboxamido)piperidine dihydrochloride saltYield 100%

Procedure

A solution of tert-butyl 4-(2-(4-(trifluoromethyl)benzyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamido)piperidine-1-carboxylate (9 in Scheme 1(c)), 340 mg, 0.6 mmol) in 4 N HCl/dioxane (10.0 mL) was allowed to stir at room temperature for 2 h. The reaction mixture was then concentrated and the resulting residue was triturated with ethyl ether to give 4-(2-(4-(trifluoromethyl)benzyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamido)piperidine dihydrochloride salt as a white solid (320 mg, 100%).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe resulting residue was triturated with ethyl ether

Sources & evidence

ORD record
ord-95d9ec7f90c14ca8a50b2f4d1c8e344b
Source dataset
uspto-grants-2013_10
Patent number
US08557822B2

Reaction notes

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