Reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.C(N(CC)CC)C.ClC(OCC)=O.[CH2:29]([C:36]1([OH:42])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][C:13]([N:39]1[CH2:38][CH2:37][C:36]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([OH:42])[CH2:41][CH2:40]1)=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2Participants
6
Procedure
To a stirred solution of 5.0 g of β-(2-methyl-3-indolyl)propionic acid and 2.5 g of triethylamine in 100 ml of chloroform was added dropwise 2.7 g of ethyl chloroformate at a temperature below 0° C. After the addition was complete, stirring was continued for additional 15 minutes and thereto was added 4.7 g of 4-benzyl-4-hydroxypiperidine in several portions. The reaction mixture was stirred for 4 hours at room temperature and allowed to stand overnight. The reaction product was washed thoroughly with water and concentrated to dryness. The residue was recrystallized from ethanol to give 1-[β-(2-methyl-3-indolyl)propionyl]-4-benzyl-4-hydroxypiperidine, melting at 117°-119° C.
Workup
- additionAfter the addition
- stirringThe reaction mixture was stirred for 4 hours at room temperature
- waitto stand overnight
- washThe reaction product was washed thoroughly with water
- concentrationconcentrated to dryness
- customThe residue was recrystallized from ethanol
Sources & evidence
- ORD record
- ord-3024e340990f494fa08720f195cbe64d
- Source dataset
- uspto-grants-1979_04
- Patent number
- US04148796
Linked notes
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