Hydrazine hydrate (1:1) → (2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl)propan-2-ol

HRID 2233367Notes

Reaction equation

HRID 2233367 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C@H:13]([OH:26])[CH2:14][N:15]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:8][CH2:7]1.O.NN>C(O)C>[NH2:15][CH2:14][C@@H:13]([OH:26])[CH2:12][N:9]1[CH2:10][CH2:11][CH:6]([O:5][C:4]2[CH:27]=[CH:28][C:29]([Cl:30])=[C:2]([Cl:1])[CH:3]=2)[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59295988(S)-2-[3-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 11151315(2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-2-[3-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione (4 g) in ethanol (100 ml) was treated with 20 ml of hydrazine monohydrate and the resulting mixture was refluxed for 3 h. The reaction was cooled and filtered. The filtrate was evaporated and the product was chromatographed (ethyl acetate) to give the title compound as a yellow oil which solidified on standing (2.5 g).

Workup

  1. temperaturethe resulting mixture was refluxed for 3 h
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe product was chromatographed (ethyl acetate)

Sources & evidence

ORD record
ord-13730ca448e94cffb915bcd1c9d523c0
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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