Water → HCID 20186020, compound
Reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][C:20]#[N:21].O>CN(C=O)C.C(O)(=O)C>[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[O:13][CH2:17][CH2:18][CH2:19][C:20]#[N:21])[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
3-(Pyrrolidinomethyl)phenol (10 g) was dissolved in DMF (50 ml). The solution was cooled in ice and sodium hydride (2.98 g) added over 45 minutes. After stirring for a further 60 minutes 4-bromobutyronitrile (6.2 ml) was added dropwise. The mixture was then stirred at room temperature for a further 40 hours. Water was added (150 ml) and the pH of the solution adjusted to about 5 with glacial acetic acid. The solution was extracted with ether (3×100 ml). The aqueous layer was adjusted to pH 10 with K2CO3 and re-extracted with chloroform (3×100 ml). The chloroform extracts were washed with water, dried (MgSO4) and evaporated to give a light brown oil (33.49 g). To remove residual DMF this oil was dissolved in ethyl acetate and the solution extracted (×6) with water. The ethyl acetate solution was finally dried (MgSO4) and evaporated to give the product as a light brown oil (11.16 g).
Workup
- temperatureThe solution was cooled in ice
- additionwas added dropwise
- extractionThe solution was extracted with ether (3×100 ml)
- extractionre-extracted with chloroform (3×100 ml)
- washThe chloroform extracts were washed with water
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-e2ea2175990d463f88bf9f514cdf1550
- Source dataset
- uspto-grants-1987_09
- Patent number
- US04694008
Reaction notes
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