Benzene → 2,2-Dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone

HRID 127482Notes

Reaction equation

HRID 127482 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]([CH2:10][NH2:11])O.C1C=CC=CC=1.[Cl:18][CH:19]([Cl:23])[C:20](Cl)=[O:21]>O>[Cl:18][CH:19]([Cl:23])[C:20]([N:11]1[C:1]2([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[O:7][CH2:8][CH2:10]1)=[O:21]

Participants

6

Reactant 4

HCID 241BenzeneHCID 700EthanolamineHCID 6593Dichloroacetyl chlorideHCID 7967Cyclohexanone

Product 1

HCID 34824022,2-Dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

From a boiling mixture of 64 g. (0.645 moles) of cyclohexanone and 30 g. (0.491 moles) of ethanolamine in 100 ml. of benzene the water formed is continuously distilled off. Boiling is continued until 8.8 ml. of water are separated. The reaction mixture is then cooled, 55 g. (0.55 moles) of a 40% aqueous sodium hydroxide solution are added followed by dropwise addition of 74 g. (0.5 moles) of dichloroacetyl chloride with external salt/ice cooling. The mixture is stirred for two additional hours at room temperature and thereafter washed with an aqueous hydrochloric acid solution and subsequently with water. From the neutral mixture obtained benzene is distilled off in vacuo. 10 g. (0.4 moles) of a greenish-white crystalline substance are obtained. Recrystallization from absolute ethanol affords a white crystalline product melting at 105.5° to 107° C. The structure of the named compound can be verified by IR spectrum analysis.

Workup

  1. additionFrom a boiling mixture of 64 g
  2. distillationis continuously distilled off
  3. customof water are separated
  4. temperatureThe reaction mixture is then cooled
  5. addition(0.55 moles) of a 40% aqueous sodium hydroxide solution are added
  6. additionfollowed by dropwise addition of 74 g
  7. washwashed with an aqueous hydrochloric acid solution and subsequently with water
  8. customFrom the neutral mixture obtained benzene
  9. distillationis distilled off in vacuo
  10. custom(0.4 moles) of a greenish-white crystalline substance are obtained
  11. customRecrystallization from absolute ethanol

Sources & evidence

ORD record
ord-ccb974662c76495f8950a96c91e44b2d
Source dataset
uspto-grants-1981_03
Patent number
US04256481

Reaction notes

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