Water → 9-(2-Phenylethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-3-one

HRID 223366Notes

Reaction equation

HRID 223366 reaction equation
[O:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][NH:4][C:3](=[O:12])[CH2:2]1.[C:13]1([CH2:19][CH2:20]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>CN(C)C=O.C(N(CC)CC)C>[C:13]1([CH2:19][CH2:20][N:9]2[CH2:8][CH2:7][C:6]3([O:1][CH2:2][C:3](=[O:12])[NH:4][CH2:5]3)[CH2:11][CH2:10]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7666Phenethyl bromideHCID 130594341-Oxa-4,9-diazaspiro(5.5)undecan-3-one

Product 1

HCID 130617319-(2-Phenylethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-3-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3.0 g of 1-oxa-4,9-diazaspiro[5.5]undecan-3-one and 5 ml of phenylethyl bromide in 60 ml of dimethylformamide and 10 ml of triethylamine was heated at 70° C. for 3 hours. The mixture was poured into water, extracted with methylene chloride and the extract was washed with water and evaporated. Crystallization of the residue from ethyl acetate gave 1.2 g of 9-(2-phenylethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-3-one, m.p. 140°-141° C. The HCl salt of 9-(2-phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-3-one was prepared by dissolving the free base in methanolic HCl and precipitating with ether, m.p. 247°-250° C.

Workup

  1. extractionextracted with methylene chloride
  2. washthe extract was washed with water
  3. customevaporated
  4. customCrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-8d3a7f9a66084af9a2943ff160d25f70
Source dataset
uspto-grants-1982_10
Patent number
US04353900

Reaction notes

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