Piperidine → Piperidine-1-propanol
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(O)C.O.Br[CH2:18][CH2:19][CH2:20][OH:21]>O.ClCCl>[N:7]1([CH2:18][CH2:19][CH2:20][OH:21])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of potassium carbonate (24.9 g) and piperidine (130 mL) in 1:1 ethanol-water (130 mL) was treated with 3-bromopropan-1-ol (25.0 g). The resulting mixture was stirred vigorously for 20 h. Dichloromethane (200 mL) and water (50 mL) were added and the aqueous phase was extracted with dichloromethane (2×100 mL). The combined organic extracts were dried (magnesium sulfate) and evaporated in vacuo. Kugelrohr distillation of the residue (5-10 mm Hg, 120° C.) gave the title compound as a colorless oil (13.9 g).
Workup
- extractionthe aqueous phase was extracted with dichloromethane (2×100 mL)
- dry with materialThe combined organic extracts were dried (magnesium sulfate)
- customevaporated in vacuo
- distillationKugelrohr distillation of the residue (5-10 mm Hg, 120° C.)
Sources & evidence
- ORD record
- ord-bfd5a02699f14d76aa3eefc852870588
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07429586B2
Reaction notes
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