Hydrochloric Acid → HCID 56637474, compound

HRID 2290470Notes

Reaction equation

HRID 2290470 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:15]=1[OH:16])[CH:8]=[CH:9][C:10](O)=[O:11])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[N:23]1([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:33][CH:32]=2)[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.P(Br)(Br)Br.Cl>N1C=CC=CC=1>[C:17]([C:14]1[CH:13]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:15]=1[OH:16])[CH:8]=[CH:9][C:10]([N:26]1[CH2:27][CH2:28][N:23]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:33][CH:32]=2)[CH2:24][CH2:25]1)=[O:11])([CH3:19])([CH3:20])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24614Phosphorus tribromideHCID 998193-(3,5-Ditert-butyl-4-hydroxyphenyl)prop-2-enoic acidHCID 20232704HCID 20232704, compound

Product 1

HCID 56637474HCID 56637474, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 14.0 g. (51 mmole) 3,5-di-tert.-butyl-4-hydroxycinnamic acid and 17.7 g. (51 mmole) ethyl 4-[2-(piperazin-1-yl)-ethyl]-phenylacetate dihydrochloride in 150 ml. anhydrous pyridine is mixed dropwise, with ice cooling, with a solution of 3.57 g. (26 mmole) phosphorus tribromide in 20 ml. pyridine. Stirring is continued for 2 hours, with ice cooling, and the reaction mixture then left to stand for 12 hours at ambient temperature, whereafter it is poured on to ice and extracted with ethyl acetate. The extracts are dried and evaporated, the residue is taken up in diethyl ether and the hydrochloride is precipitated with hydrogen chloride-containing diethyl ether. After recrystallisation from a mixture of ethanol and water, to which has been added some concentrated hydrochloric acid, there are obtained 14.5 g. (47%) of hydrochloride of the desired compound; m.p. 111°-113° C.

Workup

  1. waitthe reaction mixture then left
  2. waitto stand for 12 hours at ambient temperature, whereafter it
  3. additionis poured on to ice
  4. extractionextracted with ethyl acetate
  5. customThe extracts are dried
  6. customevaporated
  7. customthe hydrochloride is precipitated with hydrogen chloride-
  8. additioncontaining diethyl ether
  9. customAfter recrystallisation
  10. additionfrom a mixture of ethanol and water
  11. additionto which has been added some concentrated hydrochloric acid, there
  12. customare obtained 14.5 g

Sources & evidence

ORD record
ord-e21686e7472342a8baecd8e7f6efcf31
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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