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

HRID 370586Notes

Reaction equation

HRID 370586 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-hydroxypiperidine, 4.65 g (0.014 m) of 2-(6,11-dihydro-11-oxo-dibenz[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. filtrationThe yellow reaction mixture was filtered
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid

Sources & evidence

ORD record
ord-15857e8ce5374c8fa2f0ef0721bd4c97
Source dataset
uspto-grants-1985_07
Patent number
US04526891

Reaction notes

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