2-(3-(Dibenzylamino)-2-hydroxypropyl)isoindoline-1,3-dione → 1-Amino-3-(dibenzylamino)propan-2-ol

HRID 57596Notes

Reaction equation

HRID 57596 reaction equation
[CH2:1]([N:8]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:9][CH:10]([OH:23])[CH2:11][N:12]1C(=O)C2C(=CC=CC=2)C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl>[NH2:12][CH2:11][CH:10]([OH:23])[CH2:9][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 1

HCID 104086942-(3-(Dibenzylamino)-2-hydroxypropyl)isoindoline-1,3-dione

Product 1

HCID 104232791-Amino-3-(dibenzylamino)propan-2-olYield 98.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-(3-(dibenzylamino)-2-hydroxypropyl)isoindoline-1,3-dione (4.5 g, 11.25 mmol) in conc. HCl (50 mL) was stirred at 120° C. overnight. After cooling to room temperature, the mixture was filtered. And the filtrate was extracted with CHCl3. The aqueous layer was added aq. 30% NaOH until pH was above 7, then the solution was extracted with CH2Cl2, dried over Na2SO4 and concentrated to give yellow solid (3.0 g).

Workup

  1. filtrationthe mixture was filtered
  2. extractionAnd the filtrate was extracted with CHCl3
  3. additionThe aqueous layer was added aq. 30% NaOH until pH was above 7
  4. extractionthe solution was extracted with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0471a41d7d5f4fabae11fe5115d5b809
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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