Hydrazine hydrate (1:1) → 2-[4-(1,1-Diphenyl-methoxymethyl)-piperidin-1-yl]-ethylamine

HRID 1383457Notes

Reaction equation

HRID 1383457 reaction equation
[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>C(O)C>[C:29]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][NH2:18])[CH2:12][CH2:11]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 543500052-{2-[4-(1,1-Diphenyl-methoxymethyl)-piperidin-1-yl]-ethyl}-isoindole-1,3-dione

Product 1

HCID 542157402-[4-(1,1-Diphenyl-methoxymethyl)-piperidin-1-yl]-ethylamineYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-{2-[4-(1,1-Diphenyl-methoxymethyl)-piperidin-1-yl]-ethyl}-isoindole-1,3-dione (0.95 g, 2.1 mmol) was dissolved in ethanol (5 ml), followed by the addition of hydrazine hydrate (large excess, 2-3 ml). The solution was stirred at room temperature overnight. The white solid was precipitated. The white solid was filtered off and washed with small amount of ethanol. The filtrates were combined and concentrated. The resulted residue was dissolved in toluene (100 ml). The solution was washed with water (3×20 ml) and dried over anhydrous Na2SO4. After evaporated the solvent, the crude product 2-[4-(1,1-diphenyl-methoxymethyl)-piperidin-1-yl]-ethylamine was obtained (0.335 g, 49.4% yield).

Workup

  1. customThe white solid was precipitated
  2. filtrationThe white solid was filtered off
  3. washwashed with small amount of ethanol
  4. concentrationconcentrated
  5. dissolutionThe resulted residue was dissolved in toluene (100 ml)
  6. washThe solution was washed with water (3×20 ml)
  7. dry with materialdried over anhydrous Na2SO4
  8. customAfter evaporated the solvent

Sources & evidence

ORD record
ord-1855a21962764c8ca89735814e5e4e53
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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