Hydrazine hydrate (1:1) → 4-((3-(3-Aminopropyl)phenylamino)methyl)heptan-4-ol

HRID 1189958Notes

Reaction equation

HRID 1189958 reaction equation
[OH:1][C:2]([CH2:28][CH2:29][CH3:30])([CH2:25][CH2:26][CH3:27])[CH2:3][NH:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH:8]=[CH:9][CH:10]=1.O.NN>C(O)C>[NH2:14][CH2:13][CH2:12][CH2:11][C:7]1[CH:6]=[C:5]([NH:4][CH2:3][C:2]([OH:1])([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 672991752-(3-(3-(2-Hydroxy-2-propylpentylamino)phenyl)propyl)isoindoline-1,3-dione

Product 1

HCID 593170004-((3-(3-Aminopropyl)phenylamino)methyl)heptan-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(3-(3-(2-hydroxy-2-propylpentylamino)phenyl)propyl)isoindoline-1,3-dione (0.22 g, 0.71 mmol) and hydrazine hydrate (0.1 ml, 1.6 mmol) in ethanol was stirred at room temperature for 24 hours. The solvent was evaporated under reduced pressure. Purification by column chromatography (5% to 10% MeOH—CH2Cl2 gradient) gave 4-((3-(3-aminopropyl)phenylamino)methyl)heptan-4-ol as a light yellow semisolid. Yield (0.06 g, 18%); 1H NMR (400 MHz, DMSO-d6) δ 6.93 (t, J=7.6 Hz, 1H), 6.44-6.41 (m, 2H), 6.35 (d, J=7.6 Hz, 1H), 4.92 (t, J=5.2 Hz, 1H), 4.19 (bs, 1H), 2.87 (d, J=5.2 Hz, 2H), 2.54-2.50 (m, 2H), 2.44 (t, J=7.6 Hz, 2H), 1.55-1.62 (quintet, J=7.2 Hz, 2H), 1.42-1.33 (m, 4H), 1.32-1.27 (m, 4H), 0.85 (t, J=7.2 Hz, 6H); RP-HPLC (Method 3) tR=4.44 min, 97.48% (AUC); ESI MS m/z 279.31 [M+H]+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customPurification by column chromatography (5% to 10% MeOH—CH2Cl2 gradient)

Sources & evidence

ORD record
ord-85f67a1241bb46678f55ef81ec44ea96
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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