Hydrochloric Acid → HCID 56624408, compound

HRID 2290449Notes

Reaction equation

HRID 2290449 reaction equation
[N:1]1([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:18]([C:22]1[CH:23]=[C:24]([CH:30]=[C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:32]=1[OH:33])[CH:25]=[CH:26][C:27](O)=[O:28])([CH3:21])([CH3:20])[CH3:19].P(Cl)(Cl)Cl.Cl>N1C=CC=CC=1>[C:34]([C:31]1[CH:30]=[C:24]([CH:23]=[C:22]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:32]=1[OH:33])[CH:25]=[CH:26][C:27]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][CH:17]=2)[CH2:6][CH2:5]1)=[O:28])([CH3:36])([CH3:37])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24387Phosphorus trichlorideHCID 998193-(3,5-Ditert-butyl-4-hydroxyphenyl)prop-2-enoic acidHCID 2761178Ethyl 4-(piperazin-1-yl)benzoate

Product 1

HCID 56624408HCID 56624408, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 18.75 g. (80 mmole) ethyl 4-(piperazin-1-yl)-benzoate and 22.1 g. (80 mmole) 3,5-di-tert.-butyl-4-hydroxycinnamic acid in 160 ml. anhydrous pyridine is added dropwise, with ice cooling, a solution of 5.5 g. (40 mmole) phosphorus trichloride and 25 ml. anhydrous pyridine and the reaction mixture is further stirred for 1 hour with ice cooling, then poured on to ice and acidified with concentrated hydrochloric acid. The aqueous phase is extracted with ethyl acetate and the extracts are washed three times with 0.5N hydrochloric acid, dried and evaporated. The residue is recrystallised twice from a mixture of 240 ml. ethanol and 80 ml. water to give 29.2 g. (74%) of the desired product; m.p. 147°-150° C.

Workup

  1. additionpoured on to ice
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. washthe extracts are washed three times with 0.5N hydrochloric acid
  4. customdried
  5. customevaporated
  6. customThe residue is recrystallised twice from a mixture of 240 ml
  7. customwater to give 29.2 g

Sources & evidence

ORD record
ord-4438bd7b415a4be09f81afa881ac6d60
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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