Homoveratrylamine → HCID 19814324, compound

HRID 466597Notes

Reaction equation

HRID 466597 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH2:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:14]([N:21]1[CH2:32][CH2:31][C:24]2([O:28][C:27](=[O:29])[O:26][C:25]2=[CH2:30])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C(C)=CC=CC=1.CCCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]2[C:25]([OH:26])([CH3:30])[C:24]3([CH2:23][CH2:22][N:21]([CH2:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:32][CH2:31]3)[O:28][C:27]2=[O:29])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 8421HomoveratrylamineHCID 19814218HCID 19814218, compound

Product 1

HCID 19814324HCID 19814324, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8900HeptaneSolvent

Procedure

19.9 g of 2-(3,4-dimethoxyphenyl)ethylamine are portionwise added to a solution of 25.9 g of 8-benzyl-4-methylene-2-oxo-1,3-dioxa-8-azaspiro[4,5]decane in 35 ml of anhydrous xylene under stirring. Meanwhile the temperature of the reaction mixture increases to 35° to 40° C. The reaction mixture is left to stand at room temperature overnight, then the crystalline reaction mixture is diluted with n-heptane and filtered. The solid precipitate obtained is recrystallized from ethanol to obtain the title compound in 94% yield, m.p.: 181°-183° C.

Workup

  1. temperatureMeanwhile the temperature of the reaction mixture increases to 35° to 40° C
  2. waitThe reaction mixture is left
  3. filtrationfiltered
  4. customThe solid precipitate obtained
  5. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-eeeabe2351f34092821d1da0836cc939
Source dataset
uspto-grants-1992_10
Patent number
US05157038

Reaction notes

Loading…