Hydrazine hydrate (1:1) → 4-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzoic acid hydrazide

HRID 2085463Notes

Reaction equation

HRID 2085463 reaction equation
CO[C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=3)[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.O.[NH2:33][NH2:34]>CO>[CH2:16]([N:13]1[CH2:12][CH2:11][C:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([NH:33][NH2:34])=[O:31])=[CH:9][CH:8]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)[CH2:15][CH2:14]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 538358404-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzoic acid methyl ester

Product 1

HCID 442150944-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzoic acid hydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[1-benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzoic acid methyl ester (9.5 g, 22.9 mmol) in methanol (60 mL) was added hydrazine hydrate (8 mL). The reaction mixture was heated to reflux for 36 hours. The mixture was cooled to room temperature and concentrated. The residue was dissolved in toluene (50 mL) and concentrated under vacuum, and 4-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzoic acid hydrazide was obtained in quantitative yield. The residue was used in the subsequent steps without purification. 1HNMR (400 MHz, CD3OD) δ 7.82 (d, 1H), 7.67 (d, 1H), 7.39-7.05 (comp, 8H), 6.86 (d, 1H), 6.80 (s, 1H), 6.67 (d, 1H), 3.69 (s, 3H), 3.38 (s, 2H), 2.62-2.37 (comp, 8H); MS (M+1) 416.3.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 36 hours
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in toluene (50 mL)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6ad3d78f551c4216a5f6d8aad77a8c1d
Source dataset
uspto-grants-2004_04
Patent number
US06720336B2

Reaction notes

Loading…