Hydrochloric Acid → 1-(tert-Butoxycarbonyl)-4-[(4-chlorophenyl)methyl]piperidine-4-carboxylic acid

HRID 1470263Notes

Reaction equation

HRID 1470263 reaction equation
C[O:2][C:3]([C:5]1([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].O.[OH-].[Li+].Cl>O1CCOCC1.CO.O>[C:14]([O:13][C:11]([N:8]1[CH2:7][CH2:6][C:5]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 598404671-(1,1-Dimethylethyl) 4-methyl 4-[(4-chlorophenyl)methyl]-1,4-piperidinedicarboxylate

Product 1

HCID 189689961-(tert-Butoxycarbonyl)-4-[(4-chlorophenyl)methyl]piperidine-4-carboxylic acidYield 100.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(4-chlorobenzyl)piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (1.515 g, 4.117 mmol) in dioxane (20 ml), methanol (10 ml) and water (10 ml) at room temperature was added lithium hydroxide monohydrate (3.455 g, 82.341 mmol). After stirring at 50° C. for 2 days the solution was acidified to pH 6 with 2M HCl and the resulting white precipitate was extracted with diethyl ether (2×100 ml). The organic phases were combined, dried over sodium sulphate and concentrated to dryness, to give the acid as a white solid (1.460 g, 100%). LC-MS (LCT) m/z 376 [M+Na+], Rt 7.62 min.

Workup

  1. extractionthe resulting white precipitate was extracted with diethyl ether (2×100 ml)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4a13196dbf704091955137ee9bfa06ff
Source dataset
uspto-grants-2015_04
Patent number
US09006430B2

Reaction notes

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