Water → HCID 69822453, compound

HRID 1934891Notes

Reaction equation

HRID 1934891 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]1[C@H:18]3[CH2:19][C@H:15]([CH2:16][CH2:17]3)[C@@H:14]1[CH2:20][N:21]([CH3:23])[CH3:22])[CH:7]=[CH:6]2.O>CN(C=O)C>[CH3:23][N:21]([CH2:20][C@H:14]1[C@@H:15]2[CH2:19][C@@H:18]([CH2:17][CH2:16]2)[C@@H:13]1[C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11]2)[CH3:22]

Participants

4

Reactant 2

HCID 962WaterHCID 69822049HCID 69822049, compound

Product 1

HCID 69822453HCID 69822453, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(1S,2S,3S,4R)-3-(6-methoxy-2-naphthyl)bicyclo [2.2.1]hept-2-yl]-N, N-dimethyl methanamine in DMF was added sodium ethane thionyl. The mixture was heated to 100 C for 40 hours. When cool, water was added to quench the reaction. The aqueous phase was extracted with ethyl acetate. The organic phase was washed with water, brine, dried over magnesium sulfate and concentrated in-vacuo. Purification was achieved by column chromatography, using flask silica and DCMM/eOH(M/eOH,NH40H at 10%) in a ration of 10/1/0.1 for eluant. Yield (10%). ME 296 (MH+).

Workup

  1. temperatureThe mixture was heated to 100 C for 40 hours
  2. temperatureWhen cool
  3. customto quench
  4. customthe reaction
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washThe organic phase was washed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in-vacuo
  9. customPurification
  10. customYield (10%)

Sources & evidence

ORD record
ord-811b1d6e0d94421bacc3ad54b4164e4a
Source dataset
uspto-grants-2002_05
Patent number
US06384281B1

Reaction notes

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