Homovanillic Acid → HCID 178491602, compound

HRID 2225537Notes

Reaction equation

HRID 2225537 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][C:6]=1[O:15][CH3:16])(=O)C.C(O)(=O)CC1C=CC(O)=C(OC)C=1.P(Cl)(OCC)(OCC)=O.[CH3:39][N:40]([CH3:51])[CH2:41][CH2:42][NH:43][C@H:44]1[CH2:49][CH2:48][C@H:47]([CH3:50])[CH2:46][CH2:45]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C1C=CN=CC=1.CO.C(Cl)Cl.C(N(CC)CC)C>[CH3:39][N:40]([CH3:51])[CH2:41][CH2:42][N:43]([C@H:44]1[CH2:45][CH2:46][C@H:47]([CH3:50])[CH2:48][CH2:49]1)[C:12](=[O:14])[CH2:11][C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[C:6]([O:15][CH3:16])[CH:7]=1

Participants

10

Reactant 5

HCID 1738Homovanillic AcidHCID 11430Potassium CarbonateHCID 13139Diethyl chlorophosphateHCID 2264844-(Acetyloxy)-3-methoxybenzeneacetic acidHCID 178483797HCID 178483797, compound

Product 1

HCID 178491602HCID 178491602, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Using 2.3 g of (4-acetoxy-3-methoxyphenyl)acetic acid derived from homovanillic acid by the acetylation thereof, 2.8 ml of diethyl chlorophosphate, 2.7 ml of triethylamine, 100 ml of methylene chloride, 3 ml of N-(2-dimethylaminoethyl)-trans-4-methylcyclohexylamine (Example 78), 0.5 g of 4-dimethylaminopyridine, 100 ml of methanol, and 3 g of potassium carbonate, a reaction similar to that conducted in Example 75 was carried out. As a result, 1.44 g of N-(2-dimethylaminoethyl)-N-(trans-4-methylcyclohexyl)-2-(4-hydroxy-3-methoxyphenyl)acetamide (a compound of the present invention) was obtained as pale yellow crystal, which had the following physiochemical properties:

Sources & evidence

ORD record
ord-586e714f034b4fbbb2fe4399ae5bffda
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

Loading…