Ammonium Hydroxide → HCID 23294343, compound

HRID 1955182Notes

Reaction equation

HRID 1955182 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][C:24]([O:26]CC)=O)[CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+:29].[OH-]>CO>[NH2:29][C:24]([CH2:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][CH:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1)=[O:26]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 23294330HCID 23294330, compound

Product 1

HCID 23294343HCID 23294343, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-benzyl-1-(2-(3-(ethoxycarbonylmethyl)phenoxy)ethyl)piperidine (0.382 g, 1.00 mmol) in 5 mL of MeOH was added 5 mL of 30% NH4OH solution. The resulting solution was allowed to stir at rt for 12 hr. The MeOH was evaporated in vacuo and water (10 mL) was added. A colorless solid precipitated. The solid was collected by filtration and dried in vacuo giving the title product (218 mg, 62%): mp 100-101° C.; 1H NMR (CDCl3) 1.31 (m, 2 H), 1.60 (m, 1 H), 1.609 (m, 2 H), 2.04 (m, 2 H), 2.53 (d, J=6.6 Hz, 2 H), 2.80 (t, J=4.8 Hz, 2 H), 2.95 (d, J=11.4 Hz, 2 H), 3.55 (s, 2 H), 4.08 (t, J=6 Hz, 2 H), 5.35 (s, 2 H), 6.82 (m, 2 H), 7.13-7.27 (m, 6 H).

Workup

  1. customThe MeOH was evaporated in vacuo and water (10 mL)
  2. additionwas added
  3. customA colorless solid precipitated
  4. filtrationThe solid was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2b06beaa6518415588405559a0957928
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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