Hydrochloric Acid → HCID 9860514, compound

HRID 2185630Notes

Reaction equation

HRID 2185630 reaction equation
C(Cl)(Cl)=[O:2].[Cl:5][C:6]1[CH:30]=[CH:29][C:9]([CH2:10][O:11][CH:12]2[CH2:15][N:14]([CH:16](C3C=CC=CC=3)C3C=CC=CC=3)[CH2:13]2)=[CH:8][CH:7]=1.[CH2:31]([NH2:34])[CH:32]=[CH2:33].Cl>C(Cl)Cl.[Cl-].[Na+].O.O>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][O:11][CH:12]2[CH2:13][N:14]([C:16]([NH:34][CH2:31][CH:32]=[CH2:33])=[O:2])[CH2:15]2)=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 7853AllylamineHCID 543278103-(4-Chlorobenzyloxy)-1-(diphenylmethyl) azetidine

Product 1

HCID 9860514HCID 9860514, compoundYield 62.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Phosgene solution (1.75-M in toluene, 24 mmol) was added at 0° C. to a solution of compound (1) (20 mmol) in CH2Cl2 (40 mL). The reaction mixture was stirred at room temperature for 90 min, concentrated in vacuo, then redissolved in CH2Cl2 (40 mL) and treated with allylamine (42 mmol) at 0° C. The reaction was stirred for 4 h at room temperature, then water (40 mL) was added and the layers were separated. The aqueous layer was extracted with further CH2Cl2 (2×40 mL). The organic layers were washed with dilute HCl (20 mmol) and brine, dried (MgSO4) and concentrated in vacuo. The residue was triturated using diethyl ether to give the product (2) as a crystalline solid (3.5 g, 60%), m.p. 110-111° C. Found: C, 59.84; H, 6.11; N, 9.98. C14H17ClN2O2 requires: C, 59.89; H, 9.6.10; N, 9.97%.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionredissolved in CH2Cl2 (40 mL)
  3. stirringThe reaction was stirred for 4 h at room temperature
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with further CH2Cl2 (2×40 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated

Sources & evidence

ORD record
ord-47359c81d12945df8d559b28408ff52e
Source dataset
uspto-grants-2002_06
Patent number
US06403574B1

Reaction notes

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