Hydrochloric Acid → 4-amino-N-(1-(4-chlorophenyl)-4-hydroxybutyl)piperidine-4-carboxamide

HRID 423086Notes

Reaction equation

HRID 423086 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([NH:29]C(OC(C)(C)C)=O)([C:14](=[O:28])[NH:15][CH:16]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH2:17][CH2:18][CH2:19][OH:20])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C1COCC1.O1CCOCC1>[NH2:29][C:11]1([C:14]([NH:15][CH:16]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH2:17][CH2:18][CH2:19][OH:20])=[O:28])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57750344Tert-butyl 4-(tert-butoxycarbonylamino)-4-(1-(4-chlorophenyl)-4-hydroxybutylcarbamoyl)piperidine-1-carboxylate2×

Product 1

HCID 577502714-amino-N-(1-(4-chlorophenyl)-4-hydroxybutyl)piperidine-4-carboxamideYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl-4-(tert-butoxycarbonylamino)-4-(1-(4-chlorophenyl)-4-hydroxybutylcarbamoyl)piperidine-1-carboxylate (Intermediate 71) (1.98 g, 3.76 mmol) was stirred in THF (18.82 mL) and 4M hydrogen chloride (14.11 mL, 56.46 mmol) in dioxane was added with stirring. The resulting solution was stirred at ambient temperature overnight. The crude mixture was purified by SCX chromatography (eluent 20% 7N ammonia/MeOH in DCM). Pure fractions were evaporated to dryness to afford 4-amino-N-(1-(4-chlorophenyl)-4-hydroxybutyl)piperidine-4-carboxamide (1.04 g, 85%), as a colourless, transparent gum.

Workup

  1. stirringThe resulting solution was stirred at ambient temperature overnight
  2. customThe crude mixture was purified by SCX chromatography (eluent 20% 7N ammonia/MeOH in DCM)
  3. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-f078e2fe126846dd81b39a4e30d9cb59
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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