Hydrazine hydrate (1:1) → HCID 23294460, compound

HRID 1955183Notes

Reaction equation

HRID 1955183 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.O.[NH2:30][NH2:31]>CO>[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]([NH:30][NH2:31])=[O:26])[CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23294330HCID 23294330, compound

Product 1

HCID 23294460HCID 23294460, compoundYield 65%

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 hydrazine hydrate. 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 (240 mg, 65%): mp 89-91° C.; 1H NMR (CDCl3) 1.31 (m, 2 H), 1.60 (m, 1 H), 1.62 (m, 2 H), 2.04 (t, J=11.7 Hz, 2 H), 2.52 (d, J=6.9 Hz, 2 H), 2.76 (t, J=6.0 Hz, 2 H), 2.95 (d, J=11.4 Hz, 2 H), 3.53 (s, 2 H), 3.83 (bs, 2 H), 4.08 (t, J=6.3 Hz, 2 H), 6.66 (s, 1 H), 6.79 (m, 3 H), 7.12-7.27 (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-7e8d957fc0ca4a05a9cf01a4a3c921e1
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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