Boron trifluoride etherate → HCID 12834405, compound

HRID 2057759Notes

Reaction equation

HRID 2057759 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][C:6](=[C:9]2[C:15]3[CH:16]=[C:17]([C:20]([OH:22])=[O:21])[CH:18]=[CH:19][C:14]=3[CH2:13][CH2:12][C:11]3[CH:23]=[CH:24][CH:25]=[CH:26][C:10]2=3)[CH2:5][CH2:4]1.B(F)(F)F.[CH3:31][CH2:32]OCC>C(O)C>[CH3:2][N:3]1[CH2:8][CH2:7][C:6](=[C:9]2[C:15]3[CH:16]=[C:17]([C:20]([O:22][CH2:31][CH3:32])=[O:21])[CH:18]=[CH:19][C:14]=3[CH2:13][CH2:12][C:11]3[CH:23]=[CH:24][CH:25]=[CH:26][C:10]2=3)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 1290939559895-02-2

Product 1

HCID 12834405HCID 12834405, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 5.0 g 1-methyl-4-(3-carboxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene) piperidine hydrochloride in 200 ml of absolute ethanol was treated with 5 ml of boron trifluoride etherate. After stirring and refluxing for 18 hours the ethanol was evaporated in vacuo and the residue was partitioned between saturated aqueous sodium carbonate solution and ether. The ether phase was separated, washed with 3×100 ml of water, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The residue, 5.4 g of 1-methyl-4-(10,11-dihydro-3-ethoxycarbonyl-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, after recrystallization from acetonitrile had m.p. 85°-87° C.

Workup

  1. customwas evaporated in vacuo
  2. customthe residue was partitioned between saturated aqueous sodium carbonate solution and ether
  3. customThe ether phase was separated
  4. washwashed with 3×100 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue, 5.4 g of 1-methyl-4-(10,11-dihydro-3-ethoxycarbonyl-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, after recrystallization from acetonitrile

Sources & evidence

ORD record
ord-afe3edb51a2543f7a5774adfc6855b40
Source dataset
uspto-grants-1980_07
Patent number
US04212871

Reaction notes

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