1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-4-piperidinone → 4-Piperidinol, 4-(t-butyl)-1-((10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-yl)methyl)-, (+-)-

HRID 1449056Notes

Reaction equation

HRID 1449056 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH2:16][N:17]3[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:24]([Li])([CH3:27])([CH3:26])[CH3:25]>C1C=CC=CC=1>[C:24]([C:20]1([OH:23])[CH2:21][CH2:22][N:17]([CH2:16][CH:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=3[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]2=3)[CH2:18][CH2:19]1)([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 125156511-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-4-piperidinoneHCID 178418306HCID 178418306, compound

Product 1

HCID 30532464-Piperidinol, 4-(t-butyl)-1-((10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-yl)methyl)-, (+-)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Solution of 5 parts of 1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-4-piperidinone in 150 parts by volume of benzene is added dropwise over a period of 50 minutes to a stirred, cooled solution of tert-butyllithium (33.8 parts by volume of 1.9 M ethyl ether solution) in 150 parts by volume of benzene under a nitrogen atmosphere. The resultant solution is stirred at ambient temperature for about 1 hour and quenched with the addition of 100 parts by volume of 10% ammonium chloride. The solution is stirred for additional 2 hours, the organic layer separated, washed with brine, dried with magnesium sulfate and concentrated in vacuo to give clear yellow oil. This oil is chromatographed on silica gel using 1% ethanol/methylene chloride as eluent to afford 4-tert-butyl-1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-methyl]-4-piperidinol melting at about 96°-98.5° C. This compound is represented by the following general formula ##STR27##

Workup

  1. customquenched with the addition of 100 parts by volume of 10% ammonium chloride
  2. customthe organic layer separated
  3. washwashed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give clear yellow oil
  7. customThis oil is chromatographed on silica gel using 1% ethanol/methylene chloride as eluent

Sources & evidence

ORD record
ord-e2be669a4610486fa344b8190abf42fd
Source dataset
uspto-grants-1980_02
Patent number
US04188485

Reaction notes

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