Hydrazine hydrate (1:1) → 3-((3-(3-aminopropyl)phenoxy)methyl)pentan-3-OL

HRID 875513Notes

Reaction equation

HRID 875513 reaction equation
[CH2:1]([C:3]([OH:28])([CH2:26][CH3:27])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][N:15]2C(=O)C3C(=CC=CC=3)C2=O)[CH:9]=[CH:10][CH:11]=1)[CH3:2].O.NN>>[NH2:15][CH2:14][CH2:13][CH2:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[O:5][CH2:4][C:3]([OH:28])([CH2:26][CH3:27])[CH2:1][CH3:2]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 580275942-(3-(3-(2-Ethyl-2-hydroxybutoxy)phenyl)propyl)isoindoline-1,3-dione

Product 1

HCID 252557003-((3-(3-aminopropyl)phenoxy)methyl)pentan-3-OL

Procedure

Deprotection of 2-(3-(3-(2-ethyl-2-hydroxybutoxy)phenyl)propyl)isoindoline-1,3-dione using hydrazine hydrate following the method described in Example 18 gave Example 32. 1H NMR (400 MHz, DMSO-d6) δ 7.13 (t, J=6.8 Hz, 1H), 6.69-6.73 (m, 3H), 4.28 (brs, 1H), 3.66 (s, 2H), 2.99 (t, J=4.8 Hz, 2H), 2.47-2.55 (m, 4H), 1.45-1.51 (m, 4H), 0.80 (t, J=7.6 Hz, 6H).

Workup

  1. customgave Example 32

Sources & evidence

ORD record
ord-dd8a50585f3d446f98aaded0749b80a0
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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