1-Chloroethyl chloroformate → 5,6,7,8-tetrahydro-4H-furo[3,2-d]azepine

HRID 253990Notes

Reaction equation

HRID 253990 reaction equation
C([N:8]1[CH2:14][CH2:13][C:12]2[O:15][CH:16]=[CH:17][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>C(Cl)Cl.CO>[O:15]1[C:12]2[CH2:13][CH2:14][NH:8][CH2:9][CH2:10][C:11]=2[CH:17]=[CH:16]1

Participants

5

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 196001856-Benzyl-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine

Product 1

HCID 183773115,6,7,8-tetrahydro-4H-furo[3,2-d]azepine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-benzyl-5,6,7,8-tetrahydro-4H-furo[3,2-d]azepine (11.3 mmol) in methylene chloride (56 mL) is cooled to ° C. and treated with 1-chloroethyl chloroformate (ACE-Cl) (56.4 mmol). The reaction is warmed to RT for 1 hour, diluted with methylene chloride (100 mL), washed with NaHCO3 (50 mL), and extracted with methylene chloride (50 mL). The combined organic layers are washed with brine (50 mL), dried and concentrated to give an oily residue which was dissolved in methanol (150 mL) and refluxed for 1 hour. The solvent is removed in vacuo and the crude product is triturated in ether and filtered to give 5,6,7,8-tetrahydro-4H-furo[3,2-d]azepine, which is used without further purification.

Workup

  1. washwashed with NaHCO3 (50 mL)
  2. extractionextracted with methylene chloride (50 mL)
  3. washThe combined organic layers are washed with brine (50 mL)
  4. customdried
  5. concentrationconcentrated
  6. customto give an oily residue which
  7. temperaturerefluxed for 1 hour
  8. customThe solvent is removed in vacuo
  9. customthe crude product is triturated in ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-dda9767af80b4622a8e096ad3a4d2a4e
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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