Water → 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-2H-benzo[b]pyran-3-ol

HRID 1905781Notes

Reaction equation

HRID 1905781 reaction equation
[C:1]([C:3]1[CH:15]=[CH:14][C:6]2[O:7][C:8]([CH3:13])([CH3:12])[CH:9]3[O:11][CH:10]3[C:5]=2[CH:4]=1)#[N:2].[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=[O:22].[H-].[Na+].O>CS(C)=O.C(OCC)(=O)C>[C:1]([C:3]1[CH:15]=[CH:14][C:6]2[O:7][C:8]([CH3:13])([CH3:12])[C@@H:9]([OH:11])[C@H:10]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]3=[O:22])[C:5]=2[CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 126652-PiperidoneHCID 24758Sodium hydrideHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Product 1

HCID 131511766-cyano-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-2H-benzo[b]pyran-3-ol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Cyano-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-benzo[b]pyran and 2-piperidone was stirred in dimethyl sulphoxide under nitrogen at room temperature. Sodium hydride (81% dispersion in mineral oil) was added during 5 mins. and the reaction stirred for a further 6 hours. Addition of water, extraction with ethyl acetate, drying of the organic phase with magnesium sulpate, filatration, evaporation and recrystallisation from ethyl acetate gave 6-cyano-3,4-dihydro-2, 2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-2H-benzo[b]pyran-3-ol was prepared, as crystals of m.p. 155° C.

Workup

  1. dry with materialdrying of the organic phase with magnesium sulpate, filatration, evaporation and recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-980ecdeaabf14a0a853f7edd8123c14c
Source dataset
uspto-grants-1987_03
Patent number
US04647670

Reaction notes

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