Benzene → 2,2-Dichloro-1-(1-oxa-5-azaspiro[5.5]undecan-5-yl)ethan-1-one

HRID 127485Notes

Reaction equation

HRID 127485 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:8][CH2:9][CH2:10][CH2:11]O.C1C=CC=CC=1.[Cl:19][CH:20]([Cl:24])[C:21](Cl)=[O:22]>O>[Cl:19][CH:20]([Cl:24])[C:21]([N:8]1[C:1]2([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[O:7][CH2:11][CH2:10][CH2:9]1)=[O:22]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6593Dichloroacetyl chlorideHCID 7967CyclohexanoneHCID 90863-Amino-1-propanol

Product 1

HCID 132772052,2-Dichloro-1-(1-oxa-5-azaspiro[5.5]undecan-5-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

From a boiling mixture of 17.6 g. (0.18 moles) of cyclohexanone and 11.2 g. (0.15 moles) of 3-aminopropanol in 50 ml. of benzene the water formed is continuously distilled off. Boiling is continued until 2.7 ml. of water are separated. The reaction mixture is then cooled and 16 ml. (0.165 moles) of a 40% aqueous sodium hydroxide solution are added followed by a subsequent dropwise addition of 22.1 g. (0.15 moles) of dichloroacetyl chloride, with external salt/ice cooling.

Workup

  1. additionFrom a boiling mixture of 17.6 g
  2. distillationis continuously distilled off
  3. customof water are separated
  4. temperatureThe reaction mixture is then cooled
  5. addition(0.165 moles) of a 40% aqueous sodium hydroxide solution are added
  6. additionfollowed by a subsequent dropwise addition of 22.1 g

Sources & evidence

ORD record
ord-d40a2305369442aa974c6de9b8e13141
Source dataset
uspto-grants-1981_03
Patent number
US04256481

Reaction notes

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