Methanol → 4-(4-Chlorophenyl)-1-[2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl]-4-hydroxypiperidine

HRID 580047Notes

Reaction equation

HRID 580047 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CS(O[CH2:20][CH2:21][C:22]1[CH:37]=[CH:36][C:25]2[O:26][CH2:27][C:28]3[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=3[C:30](=[O:31])[C:24]=2[CH:23]=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].CO>CCOCC.C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:9][CH2:10][N:11]([CH2:20][CH2:21][C:22]3[CH:37]=[CH:36][C:25]4[O:26][CH2:27][C:28]5[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=5[C:30](=[O:31])[C:24]=4[CH:23]=3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 108064742-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethanol methanesulfonate

Product 1

HCID 134771154-(4-Chlorophenyl)-1-[2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl]-4-hydroxypiperidineYield 35%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3 g (0.014 m) of 4-(4-chlorophenyl)-4-hydroxypiperdine, 4.65 g (0.014 m) of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethanol methanesulfonate of Example 1, 1.96 g (0.014 m) of K2CO3, 30 ml of methanol and 30 ml of absolute ethanol was refluxed overnight. The yellow reaction mixture was filtered and evaporated. The residue was partitioned between ethyl acetate and water. The organic phase was dried (Na2SO4), filtered and evaporated to afford a solid. Trituration with ether gave 2.17 g (35%) of 4-(4-chlorophenyl)-1-[2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl]-4-hydroxypiperidine, m.p. 151°-153° C.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe yellow reaction mixture was filtered
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and water
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a solid

Sources & evidence

ORD record
ord-86f45e9bfb154825a194a6dbe9e68a6c
Source dataset
uspto-grants-1988_06
Patent number
US04751238

Reaction notes

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