Hydrazine → N-(3-(1-[(3S)-3-amino-3-phenylpropyl]-4-piperidinyl)phenyl)-2-methylpropanamide

HRID 1832211Notes

Reaction equation

HRID 1832211 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C@H:12]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:22]=[C:23]([NH:27][C:28](=[O:32])[CH:29]([CH3:31])[CH3:30])[CH:24]=[CH:25][CH:26]=2)[CH2:17][CH2:16]1.NN>C(O)C>[NH2:3][C@H:12]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:22]=[C:23]([NH:27][C:28](=[O:32])[CH:29]([CH3:31])[CH3:30])[CH:24]=[CH:25][CH:26]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 60078705N-(3-{1-[(3S)-3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-YL)-3-phenylpropyl]-4-piperidinyl}phenyl)-2-methylpropanamide

Product 1

HCID 69523474N-(3-(1-[(3S)-3-amino-3-phenylpropyl]-4-piperidinyl)phenyl)-2-methylpropanamideYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(3-{1-[(3S)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl]-4-piperidinyl}phenyl)-2-methylpropanamide (4.60 g, 9.06 mmol) and hydrazine (3.62 g, 72.4 mmol) in ethanol (150 mL) was refluxed for 12 h. The resulting white precipitate was filtered out and the filtrate was concentrated under vacuum. The residue was washed with CH2Cl2/EtOAc. (1:1, 3×50 mL) and the combined organic fractions were concentrated in vacuo to give the desired product (2.90 g, 95%). 1H NMR (400 MHz, CDCl3) δ 7.45 (s, 1H), 7.39–7.30 (m, 6H), 7.297.19 (m, 2H), 6.95 (d, 1H, J=7.2), 4.01 (t, 1H, J=6.8 Hz), 3.04 (t, 2H, J=10.6 Hz), 2.62–2.30 (m, 6H) 2.05–1.70 (m, 8H), 1.24 (d, 6H, J=6.8 Hz); ESMS m/e: 380.4 (M+H)+.

Workup

  1. temperaturewas refluxed for 12 h
  2. filtrationThe resulting white precipitate was filtered out
  3. concentrationthe filtrate was concentrated under vacuum
  4. washThe residue was washed with CH2Cl2/EtOAc
  5. concentration(1:1, 3×50 mL) and the combined organic fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-d59f851599984370b646c2ffbf5ab099
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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