Hydrochloric Acid → 4-(((1-(Tert-butoxycarbonyl)piperidin-4-yl)(4-chlorophenethyl)amino)methyl)benzoic acid

HRID 59796Notes

Reaction equation

HRID 59796 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][CH2:7][N:8]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([O:31]C)=[O:30])=[CH:25][CH:24]=2)[CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[C:18]([O:17][C:15]([N:12]1[CH2:11][CH2:10][CH:9]([N:8]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]([OH:31])=[O:30])=[CH:27][CH:28]=2)[CH2:7][CH2:6][C:5]2[CH:33]=[CH:34][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:14][CH2:13]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 121422786tert-Butyl 4-((4-chlorophenethyl)(4-(methoxycarbonyl)benzyl)amino)piperidine-1-carboxylate

Product 1

HCID 1214102754-(((1-(Tert-butoxycarbonyl)piperidin-4-yl)(4-chlorophenethyl)amino)methyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

tert-Butyl 4-((4-chlorophenethyl)(4-(methoxycarbonyl)benzyl)amino)piperidine-1-carboxylate obtained in Step 1 was dissolved in MeOH (5 mL/mmol), NaOH (5 eqs) (as a 0.5 N aqueous solution) was added and the reaction mixture was stirred at room temperature for 15 hours.). pH of the reaction was made neutral by careful addition of 0.5 N HCl, and methanol was removed in vacuo. The precipitated product was filtered off, washed several times with acetone/diethyl ether mixture (1:2 v/v) and dried in the air. It was found to be of sufficient purity to be used in the next step without further purification.

Workup

  1. customwas removed in vacuo
  2. filtrationThe precipitated product was filtered off
  3. washwashed several times with acetone/diethyl ether mixture (1:2 v/v)
  4. customdried in the air
  5. customto be used in the next step without further purification

Sources & evidence

ORD record
ord-5e8eec4326744e10b0337d88a1ebce05
Source dataset
uspto-grants-2016_09
Patent number
US09440953B2

Reaction notes

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