Triethylamine → 4-Benzyl-2-(2-chloroethyl)-2,3-dihydro-1,4-benzoxazepin-5(4H)-one

HRID 4799Notes

Reaction equation

HRID 4799 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16](O)=[O:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.S(Cl)([Cl:32])=O>>[CH2:1]([N:8]1[C:16](=[O:17])[C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[O:13][CH:10]([CH2:11][CH2:12][Cl:32])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 212714812-[(1-Benzyl-3-pyrrolidinyl)oxy]-benzoic acid

Product 1

HCID 137262924-Benzyl-2-(2-chloroethyl)-2,3-dihydro-1,4-benzoxazepin-5(4H)-one

Procedure

To 85.7 g (0.29 mole) of 2-[(1-benzyl-3-pyrrolidinyl)oxy]-benzoic acid was added 150 ml of thionyl chloride. The solution stood for 15 min and was then refluxed 30 min. and concentrated in vacuo. The residue was twice treated with 250 ml of chloroform and concentrated in vacuo. The residue was dissolved in 500 ml of chloroform and 101 g (1 mole) of triethylamine added slowly with stirring. The solution was refluxed 1 hr. and concentrated in vacuo. The residue was partitioned between 50% ethyl acetate-50% isopropyl ether and dilute hydrochloric acid. The organic layer was washed with dilute sodium hydroxide and concentrated. The residue was crystallized 5 times from isopropyl ether-ethyl acetate. Yield of product was 23.8 g (26%), m.p. 145.0°-147° C.

Workup

  1. temperaturewas then refluxed 30 min.
  2. concentrationconcentrated in vacuo
  3. additionThe residue was twice treated with 250 ml of chloroform
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in 500 ml of chloroform
  6. temperatureThe solution was refluxed 1 hr
  7. concentrationand concentrated in vacuo
  8. customThe residue was partitioned between 50% ethyl acetate-50% isopropyl ether and dilute hydrochloric acid
  9. washThe organic layer was washed with dilute sodium hydroxide
  10. concentrationconcentrated
  11. customThe residue was crystallized 5 times from isopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-cff393a1d9df4371b88ee0b282584eb9
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Reaction notes

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