Dimethylformamide → 1-Phenylmethyl-alpha,alpha-dimethyl-1,2,3,6-tetrahydro-4-pyridine-acetic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([C:8]1(O)[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)([CH3:7])[CH3:6])[CH3:2].S(Cl)(Cl)=O.CN(C)C=O>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:22])[C:5]([C:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]=1)([CH3:7])[CH3:6])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Step B To a solution of 2-(1-benzyl-4-hydroxy-piperidin-4-yl)-2-methyl-propionic acid ethyl ester (18.5 g, 61 mmol) in chloroform (75 mL) was added thionyl chloride (8.9 mL, 120 mmol) and dimethylformamide (0.17 mL). The reaction mixture was heated at 100° C. for 18 h, then cooled to room temperature and concentrated. To the resulting residue was added aqueous NaOH solution (10 N) to adjust the “pH” of the mixture to basic. The mixture was then extracted with ethyl ether twice. The combined organic extracts were washed with water, brine, dried over MgSO4, and concentrated to give 2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-methyl-propionic acid ethyl ester as a brown oil (13 g, 75%).
Workup
- temperaturecooled to room temperature
- concentrationconcentrated
- additionTo the resulting residue was added aqueous NaOH solution (10 N)
- extractionThe mixture was then extracted with ethyl ether twice
- washThe combined organic extracts were washed with water, brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-38bafdb7bf13470a96236f262f3db898
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354444B2
Reaction notes
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