Hydrochloric Acid → 1-Phenyl-1-(piperidin-3-yl)heptan-1-ol

HRID 2355308Notes

Reaction equation

HRID 2355308 reaction equation
[OH:1][C:2]([CH:15]1[CH2:20][CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl>CC#N>[C:9]1([C:2]([CH:15]2[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]2)([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59382974Tert-butyl 3-(1-hydroxy-1-phenylheptyl)piperidine-1-carboxylate

Product 1

HCID 593829241-Phenyl-1-(piperidin-3-yl)heptan-1-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tert-Butyl 3-(1-hydroxy-1-phenylheptyl)piperidine-1-carboxylate, obtained as described above, in CH3CN (40 mL) and 2 N HCl (40 mL) was vigorously stirred at rt for 20 h. 60 mL of the reaction mixture was quenched with saturated NaHCO3, extracted three times with EtOAc, and dried over Na2SO4. The crude product (0.2709 g, 80% in two steps) was used without further purification. LC-MS (3 min) tR=1.29 min in 3 min chromatography, m/z 276 (MH+).

Workup

  1. customobtained
  2. custom60 mL of the reaction mixture was quenched with saturated NaHCO3
  3. extractionextracted three times with EtOAc
  4. dry with materialdried over Na2SO4
  5. customThe crude product (0.2709 g, 80% in two steps) was used without further purification

Sources & evidence

ORD record
ord-fa100a2f81a54094a4d8221516c73e01
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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