Hydrochloric Acid → HCID 13531607, compound

HRID 370470Notes

Reaction equation

HRID 370470 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([N+:11]([O-:13])=[O:12])=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[CH:20]=1.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[ClH:28].[OH2:29]>C(OCC)C.C(O)(C)C.C(O)C>[OH2:10].[OH2:29].[ClH:28].[ClH:28].[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:2][C:3]2[CH:4]=[CH:5][C:6]3[O:10][C:9]([N+:11]([O-:13])=[O:12])=[C:8]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:7]=3[CH:20]=2)[CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 531671-MethylpiperazineHCID 13531604HCID 13531604, compound

Product 1

HCID 13531607HCID 13531607, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

A stirred mixture of 5 g. (0.015 mole) of 5-bromomethyl-2-nitro-3-phenylbenzofuran and 7.5 g. (0.075 mole) of N-methylpiperazine in 15 ml. of ethanol is heated at 45° C. for 1 hour. The reaction mixture is evaporated to provide a residue which is extracted with diethyl ether. The ether extracts are washed with water and with a saturated sodium chloride solution and dried. Evaporation of the ether solution provides a yellow oil which is dissolved in diethyl ether and treated while stirring with a solution of 4N hydrochloric acid in isopropanol until the reaction is complete. The solid is stirred in hot ethanol while adding water until it is all in solution. Cooling provides a fluffy yellow product, 1-methyl-4-(2-nitro-3-phenyl-5-benzofuranylmethyl)piperazine dihydrochloride dihydrate, m.p. 269°-276° C. (dec.), having the structure ##STR8##

Workup

  1. additionA stirred mixture of 5 g
  2. customThe reaction mixture is evaporated
  3. customto provide a residue which
  4. extractionis extracted with diethyl ether
  5. washThe ether extracts are washed with water and with a saturated sodium chloride solution
  6. customdried
  7. customEvaporation of the ether solution
  8. customprovides a yellow oil which
  9. additiontreated
  10. temperatureCooling

Sources & evidence

ORD record
ord-54a7b7453f644003a886ab638874ccf6
Source dataset
uspto-grants-1985_07
Patent number
US04526896

Reaction notes

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