Cyproheptadine → HCID 131716035, compound

HRID 1722824Notes

Reaction equation

HRID 1722824 reaction equation
[S:1](Cl)([Cl:4])(=[O:3])=[O:2].C(Cl)Cl.[CH2:9]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN1C[CH2:42][C:26](=[C:27]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=C[C:33]3[C:28]2=CC=C[CH:32]=3)CC1>C(N(CC)CC)C>[ClH:4].[CH:33]1[C:28]2[CH2:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:27]=2[CH:26]=[CH:42][C:32]=1[S:1]([N:19]1[CH2:20][CH2:21][N:16]([CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:17][CH2:18]1)(=[O:3])=[O:2]

Participants

6

Reactant 4

HCID 2913CyproheptadineHCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 759941-Benzylpiperazine

Product 1

HCID 131716035HCID 131716035, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound is prepared by adding to a stirred solution of the above sulfonyl chloride intermediate (4 g, 0.015 mol) in 50 mL of methylene chloride (2.7 g, 0.015 mol), 1-(benzyl)piperazine (2.7 g, 0.015 mol) and triethylamine (6 mL). The reactin mixture is stirred overnight and the methylene chloride layer is washed with water and dried over anhydrous Na2SO4. Evaporation of the methylene chloride under reduced pressure affords crude product which is purified by HPLC using silica gel column and ethyl acetate as the eluent. The desired fractions (Rf =0.8) are evaporated to give pure free base which is converted to the hydrochloride salt; m.p. 274°-275° C. (33% yield).

Workup

  1. washthe methylene chloride layer is washed with water
  2. dry with materialdried over anhydrous Na2SO4
  3. customEvaporation of the methylene chloride under reduced pressure
  4. customaffords crude product which
  5. customis purified by HPLC
  6. customThe desired fractions (Rf =0.8) are evaporated
  7. customto give pure free base which

Sources & evidence

ORD record
ord-4294d06dfd514258bde13d3a2d652685
Source dataset
uspto-grants-1989_08
Patent number
US04857644

Reaction notes

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