Potassium Carbonate → HCID 178490510, compound

HRID 2225523

Reaction equation

HRID 2225523 reaction equation
C([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([OH:13])=O)=[CH:7][C:6]=1[O:16][CH3:17])(=O)C.P(Cl)(OCC)(OCC)=O.[CH3:27][N:28]([CH3:39])[CH2:29][CH2:30][NH:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([CH3:38])[CH2:34][CH2:33]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C1C=CN=CC=1.CO.C(Cl)Cl.C(N(CC)CC)C>[CH3:27][N:28]([CH3:39])[CH2:29][CH2:30][N:31]([C@H:32]1[CH2:33][CH2:34][C@H:35]([CH3:38])[CH2:36][CH2:37]1)[C:11](=[O:13])[CH:10]=[CH:9][C:8]1[CH:14]=[CH:15][C:5]([OH:4])=[C:6]([O:16][CH3:17])[CH:7]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 13139Diethyl chlorophosphateHCID 757754-Acetoxy-3-methoxy-cinnamic acidHCID 178483797HCID 178483797, compound

Product 1

HCID 178490510HCID 178490510, compound

Reagents, catalysts & solvents 4

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

Procedure

Using 2.5 g of 4-acetoxy-3-methoxycinnamic acid, 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 73 was carried out. As a result, 1.8 g of N-(2-dimethylaminoethyl)-N-(trans-4-methylcyclohexyl)-4-hydroxy-3-methoxycinnamamide (a compound of the present invention) was obtained as white crystal, which had the following physiochemical properties:

Workup

  1. customa reaction similar to

Sources & evidence

ORD record
ord-14b7194a52b14ed78fa1f55dbebb07b1
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Linked notes

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