Chloride → HCID 178461363, compound

HRID 2225554Notes

Reaction equation

HRID 2225554 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][CH:6]=1)(=O)C.[CH:16]1[C:21](/[CH:22]=C/C(O)=O)=[CH:20][CH:19]=[C:18](O)[CH:17]=1.P(Cl)(OCC)(OCC)=O.[Cl-].C(=O)([O-])[O-].[K+].[K+].C([N:46](CC)CC)C>CN(C)C1C=CN=CC=1.CO.C(Cl)Cl>[CH3:22][C@H:21]1[CH2:20][CH2:19][C@H:18]([NH:46][C:11](=[O:13])[CH:10]=[CH:9][C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:15][CH:14]=2)[CH2:17][CH2:16]1

Participants

10

Reactant 6

HCID 312ChlorideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 13139Diethyl chlorophosphateHCID 85857Cinnamic acid, p-hydroxy-, acetateHCID 637542P-Coumaric Acid

Product 1

HCID 178461363HCID 178461363, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2.7 g of 4-acetoxycinnamic acid derived from p-coumaric acid by the acetylation thereof, 2.8 ml of diethyl chlorophosphate, 3.9 ml of triethylamine, 2 g of trans-4-methylcyclohexylammmonium chloride, 60 ml of methylene chloride, 0.6 g of 4-dimethylaminopyridine, 100 ml of methanol, and 5 g of potassium carbonate, a reaction similar to that conducted in Example 121 was carried out. The product obtained was recrystallized from methylene chloride/hexane, yielding 2.83 g of N-(trans-4-methylcyclohexyl)-4-hydroxycinnamamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. customThe product obtained
  2. customwas recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-24cd35bdbcfb4c268078a20ba3c6faf0
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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