Methanol → 3-(2-methoxyethoxy)azetidine hydrochloride

HRID 82990Notes

Reaction equation

HRID 82990 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][CH2:26][CH2:27][O:28][CH3:29])[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>ClCCCl>[ClH:1].[CH3:29][O:28][CH2:27][CH2:26][O:25][CH:23]1[CH2:24][NH:21][CH2:22]1

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 671545481-Benzhydryl-3-(2-methoxyethoxy)-azetidine

Product 1

HCID 178173733-(2-methoxyethoxy)azetidine hydrochlorideYield 92.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

1-Chloroethyl chloroformate (102 μL, 0.9 mmol) was added to a solution of 1-benzhydryl-3-(2-methoxyethoxy)-azetidine (215 mg, 0.7 mmol) in 1,2-dichloroethane (3 mL) at room temperature. The reaction mixture was then heated up to 70° C. and stirred for 2.5 hours. After cooling down to room temperature, methanol (3 mL) was added and the reaction mixture was stirred overnight at 70° C. The mixture was then concentrated to dryness and the residue was triturated in pentane (2×15 mL) to give a yellow oil (109 mg, 90%) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling down to room temperature
  2. stirringthe reaction mixture was stirred overnight at 70° C
  3. concentrationThe mixture was then concentrated to dryness
  4. customthe residue was triturated in pentane (2×15 mL)

Sources & evidence

ORD record
ord-80fd046129de4132affbb0a0bfc861b3
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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