Hydrochloric Acid → (2R)-1-[4-(2-aminoethyl)piperazinyl]-3-(2-methylbenzothiazol-5-yloxy)propan-2-ol

HRID 855581Notes

Reaction equation

HRID 855581 reaction equation
[OH:1][CH:2]([CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]2[S:32][C:31]([CH3:33])=[N:30][C:29]=2[CH:34]=1)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2C(=O)C3C=CC=CC=3C2=O)[CH2:6][CH2:5]1.O.NN.Cl>CO>[NH2:12][CH2:11][CH2:10][N:7]1[CH2:8][CH2:9][N:4]([CH2:3][C@@H:2]([OH:1])[CH2:23][O:24][C:25]2[CH:26]=[CH:27][C:28]3[S:32][C:31]([CH3:33])=[N:30][C:29]=3[CH:34]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 21935514HCID 21935514, compound

Product 1

HCID 58714341(2R)-1-[4-(2-aminoethyl)piperazinyl]-3-(2-methylbenzothiazol-5-yloxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(2-{4-[2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}ethyl)benzo[c]azoline-1,3-dione (101 mg, 0.21 mmol) in MeOH (0.84 mL) was treated with hydrazine hydrate (0.07 mL) and stirred at RT for 14 hours. HCl (1 mL, conc) was added and the solution was heated to 88° C. for 14 hours. Upon cooling, the resulting solid was filtered off and washed with H2O and EtOAc. The filtrate was pH adjusted to >12 (NaOH) and extracted with EtOAc. The combined organic layers were then concentrated to afford (2R)-1-[4-(2-aminoethyl)piperazinyl]-3-(2-methylbenzothiazol-5-yloxy)propan-2-ol as an oil.

Workup

  1. temperaturethe solution was heated to 88° C. for 14 hours
  2. temperatureUpon cooling
  3. filtrationthe resulting solid was filtered off
  4. washwashed with H2O and EtOAc
  5. extractionextracted with EtOAc
  6. concentrationThe combined organic layers were then concentrated

Sources & evidence

ORD record
ord-e9094c6d1eb2474c9ac7773a1e2c08f7
Source dataset
uspto-grants-2007_08
Patent number
US07262198B2

Reaction notes

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