Methane → alpha-[1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinyl]-alpha-phenyl-2-benzothiazolemethanol

HRID 1491690Notes

Reaction equation

HRID 1491690 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:14][CH2:13]1)=[O:11].[C:28]1([Li])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C>O1CCCC1.C1CCCCC1.C(OCC)C.C(Cl)Cl>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][N:15]2[CH2:16][CH2:17][CH:12]([C:10]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[OH:11])[CH2:13][CH2:14]2)=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 297MethaneHCID 9842862[2-Benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl)methanoneHCID 178506676HCID 178506676, compound

Product 1

HCID 18930344alpha-[1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinyl]-alpha-phenyl-2-benzothiazolemethanol

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 21895417Cyclohexane diethyletherSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve [2-benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone (2.0 g, 5.26 mmol) in anhydrous tetrahydrofuran (50 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, phenyllithium (3.16 mL of a 2.0M solution in cyclohexane/ethyl ether, 6.31 mmol). Stir at -78° C. for 30 minutes, quench with saturated ammonium chloride (100 mL), separate the organic phase and extract the aqueous phase with ethyl acetate. Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (75% ethyl acetate/hexane) to give a yellow oil. Dissolve the oil in methylene chloride and treat with activated charcoal. Filter and evaporate the solvent in vacuo to give the title compound as a white electrostatic powder; mp 67°-70° C.

Workup

  1. customquench with saturated ammonium chloride (100 mL)
  2. customseparate the organic phase
  3. extractionextract the aqueous phase with ethyl acetate
  4. dry with materialdry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customPurify by chromatography (75% ethyl acetate/hexane)
  7. customto give a yellow oil
  8. filtrationFilter
  9. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-0d0604226d51409ea9040db17bf6b9b0
Source dataset
uspto-grants-1994_12
Patent number
US05371093

Reaction notes

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