Water → 2,3-Dihydro-3,3-dimethyl-2-piperidinobenzofuran-5-yl methanesulphonate
Reaction equation
[CH3:1][C:2]1([CH3:18])[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[O:4][CH:3]1[N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>N1C=CC=CC=1>[CH3:19][S:20]([O:11][C:8]1[CH:9]=[CH:10][C:5]2[O:4][CH:3]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[C:2]([CH3:18])([CH3:1])[C:6]=2[CH:7]=1)(=[O:22])=[O:21]Participants
5
Conditions
- Temperature
- 10 °C
Procedure
To a stirred solution of 2,3-dihydro-3,3-dimethyl-5-hydroxy-2-piperidino-benzofuran (640 parts) in dry pyridine (1000 parts) at 5°-10° C was added methanesulphonyl chloride (370 parts) over 1 hour. The mixture was stirred for a further 5 hours at about 10° C, then poured into water. The precipitated gum was washed with water (3 × 200 parts) by decantation, then triturated with ethanol (500 parts) when it set to a crystalline moss which was broken up, filtered, and the residue of crude ester was washed with aqueous ethanol (2:1) and sucked dry. Drying at 35° C in vacuo over phosphoric oxide gave 2,3-dihydro-3,3-dimethyl-2-piperidinobenzofuran-5-yl methanesulphonate (660 parts, 78%) m.p. 97°-8° C.
Workup
- washThe precipitated gum was washed with water (3 × 200 parts) by decantation
- customtriturated with ethanol (500 parts) when it
- filtrationfiltered
- washthe residue of crude ester was washed with aqueous ethanol (2:1)
- customsucked dry
- dry with materialDrying at 35° C in vacuo over phosphoric oxide
Sources & evidence
- ORD record
- ord-72e38af263ae49259c3cd1fda8389729
- Source dataset
- uspto-grants-1977_09
- Patent number
- US04051154
Reaction notes
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