Hydrochloric Acid → N-Cyclopropyl-2-(4-piperidin-4-yl-phenyl)-propionamide

HRID 409727Notes

Reaction equation

HRID 409727 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]([C:22](=[O:27])[NH:23][CH:24]3[CH2:26][CH2:25]3)[CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO>[CH:24]1([NH:23][C:22](=[O:27])[CH:20]([C:17]2[CH:18]=[CH:19][C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:15][CH:16]=2)[CH3:21])[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 866861144-[4-(1-Cyclopropylcarbamoyl-ethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86686115N-Cyclopropyl-2-(4-piperidin-4-yl-phenyl)-propionamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To 3.40 g (9.13 mmol) 4-[4-(1-cyclopropylcarbamoyl-ethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (X.1) in 20 mL methanol are added 10.9 mL (13.7 mmol) 1.25 M HCl in methanol. The mixture is stirred for 12 h at rt. After that time, 2.0 mL 1.25 M HCl in methanol are added and the mixture is stirred for 2 d at 40° C. After that time, the solvent is evaporated, the residue taken up in 1N NaOH and extracted with EtOAc. After drying over sodium sulphate, the solvent is removed in vacuo to yield the desired product.

Workup

  1. stirringthe mixture is stirred for 2 d at 40° C
  2. customAfter that time, the solvent is evaporated
  3. extractionextracted with EtOAc
  4. dry with materialAfter drying over sodium sulphate
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-b3bea38a241746e1a4060bb94f502d1c
Source dataset
uspto-grants-2014_06
Patent number
US08759528B2

Reaction notes

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