Hydrochloric Acid → 4-{4-[2-Chloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-1-piperazinyl}-2-butyn-1-ol hydrochloride

HRID 866610Notes

Reaction equation

HRID 866610 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[O:6][C:7]3[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=3[CH:9]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:10][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl[CH2:32][C:33]#[C:34][CH2:35][OH:36].Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[O:6][C:7]3[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=3[CH:9]([N:11]3[CH2:12][CH2:13][N:14]([CH2:32][C:33]#[C:34][CH2:35][OH:36])[CH2:15][CH2:16]3)[CH2:10][C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 2027752-Butyn-1-ol, 4-chloro-HCID 227679431-[2-Chloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-piperazine

Product 1

HCID 227678994-{4-[2-Chloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-1-piperazinyl}-2-butyn-1-ol hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

6 G. of 1-[2-chloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-piperazine are dissolved in 65 ml. of ethanol. Subsequently, there are added successively 2.7 g. of sodium carbonate, 0.27 g. of sodium iodide. Then, a solution of 2.4 g. of 4-chloro-2-butyn-1-ol in 15 ml. of ethanol is added dropwise. The mixture is stirred for 16 hours at room temperature and thereafter for 3.5 hours at 40° C. The ethanol is then evaporated under reduced pressure and the residue partitioned between water and chloroform. The phases are separated, the aqueous solution is extracted with water and the chloroform extracts are washed with water. The solvent is evaporated, the residue dissolved in benzene and chromatographed over 140 g. of silica gel. Elution is carried out first with benzene. The 4-{4-[2-chloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-1-piperazinyl}-2-butyn-1-ol is eluted with benzene/methanol (99:1), which is obtained as an oil and is converted to the hydrochloride using the calculated amount of hydrogen chloride in ethanol. The hydrochloride crystallizes by the addition of ether; melting point 194°-195° C. (with decomposition).

Workup

  1. additionSubsequently, there are added successively 2.7 g
  2. waitfor 3.5 hours at 40° C
  3. customThe ethanol is then evaporated under reduced pressure
  4. customthe residue partitioned between water and chloroform
  5. customThe phases are separated
  6. extractionthe aqueous solution is extracted with water
  7. washthe chloroform extracts are washed with water
  8. customThe solvent is evaporated
  9. dissolutionthe residue dissolved in benzene
  10. customchromatographed over 140 g
  11. washElution
  12. washThe 4-{4-[2-chloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-1-piperazinyl}-2-butyn-1-ol is eluted with benzene/methanol (99:1)
  13. customwhich is obtained as an oil
  14. customThe hydrochloride crystallizes by the addition of ether

Sources & evidence

ORD record
ord-27291858ae3e4512a254a9ad73dfd3e3
Source dataset
uspto-grants-1978_07
Patent number
US04100173

Reaction notes

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