Dichloromethane → 3-Methyl-8-benzyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one

HRID 127266Notes

Reaction equation

HRID 127266 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:17])([CH2:14][NH:15][CH3:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.[C:21](Cl)(Cl)=[O:22].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:16][N:15]1[CH2:14][C:11]2([CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)[O:17][C:21]1=[O:22]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 183513291-Benzyl-4-((methylamino)methyl)piperidin-4-ol

Product 1

HCID 202864903-Methyl-8-benzyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 23 g 1-benzyl-4-hydroxy-4-methylaminomethylpiperidine and 250 ml dichloromethane is mixed with 100 ml of a 15% solution of phosgene in toluene. Evaporation of solvent gives a residue which is treated with 300 ml dichloromethane and 300 ml aqueous sodium bicarbonate. Separation of the dichloromethane layer followed by evaporation gives 20 g 3-methyl-8-benzyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one, mp 137°-138°.

Workup

  1. customEvaporation of solvent
  2. customgives a residue which
  3. customSeparation of the dichloromethane layer
  4. customfollowed by evaporation

Sources & evidence

ORD record
ord-0372e8c34f9c4ccdb644b6a7d2498417
Source dataset
uspto-grants-1981_03
Patent number
US04255432

Reaction notes

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