Methanol → 3-(3-Methoxypropoxy)azetidine hydrochloride

HRID 633947Notes

Reaction equation

HRID 633947 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>ClCCCl>[ClH:1].[CH3:30][O:29][CH2:28][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 67154624HCID 67154624, compound

Product 1

HCID 671544823-(3-Methoxypropoxy)azetidine hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

1-Chloroethyl chloroformate (210 μL, 1.9 mmol) was added to a solution of 1-benzhydryl-3-(3-methoxypropoxy)-azetidine (460 mg, 1.5 mmol) in 1,2-dichloroethane (7 mL) at room temperature. The reaction mixture was then heated up to 70° C. and stirred for 1.5 hours. After cooling down to room temperature, methanol (7 mL) was added and the mixture was again warmed up to 70° C. and stirred for an additional 2 hours. After concentration to dryness, the crude was triturated in pentane (2×10 mL) to afford a yellow oil (247 mg, 92%) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling down to room temperature
  2. temperaturethe mixture was again warmed up to 70° C.
  3. stirringstirred for an additional 2 hours
  4. concentrationAfter concentration to dryness
  5. customthe crude was triturated in pentane (2×10 mL)

Sources & evidence

ORD record
ord-69b68423ecc94abcabd66c976af0d403
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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