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

HRID 271240Notes

Reaction equation

HRID 271240 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-de7a08fe81484cee8caefb88276cf0f3
Source dataset
uspto-grants-2008_11
Patent number
US07452889B2

Reaction notes

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