Cyanogen Bromide → HCID 20344056, compound

HRID 2049688Notes

Reaction equation

HRID 2049688 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:13]3([C:20](=[O:21])[C:4]=2[CH:3]=1)[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3.[N:24]#CBr.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:19]([N:16]1[CH2:17][CH2:18][C:13]2([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[S:6][C:5]3[CH:22]=[CH:23][C:2]([F:1])=[CH:3][C:4]=3[C:20]2=[O:21])[CH2:14][CH2:15]1)#[N:24]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 20344029HCID 20344029, compound

Product 1

HCID 20344056HCID 20344056, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3.0 g of 2-fluoro-10,11-dihydro-1'-methyl-11-oxospiro[dibenz(b,f)thiepin-10,4'-piperidine], free base of Example 26, in 10 ml of methylene chloride is added portionwise to a mixture of 1.3 g of cyanogen bromide and 6.4 g of potassium carbonate in 17 ml of methylene chloride. After total addition, the mixture is stirred at reflux for 2 hours and then permitted to cool to ambient temperature. Thereafter, the mixture is filtered and then evaporated to dryness and the residue is taken up in methyl alcohol. The alcoholic solution is refluxed before the addition of acetone and ether, effecting a precipitate. The mixture is filtered and the supernatant liquid is evaporated. The residue is chromatographed through a silica gel column and eluted with an ether-methylene chloride (1:1) mixture, to provide 1'-cyano-2-fluoro-10,11-dihydro-11-oxospiro[dibenz(b,f)thiepin-10,4'-piperidine].

Workup

  1. additionAfter total addition
  2. temperatureat reflux for 2 hours
  3. filtrationThereafter, the mixture is filtered
  4. customevaporated to dryness
  5. temperatureThe alcoholic solution is refluxed before the addition of acetone and ether
  6. filtrationThe mixture is filtered
  7. customthe supernatant liquid is evaporated
  8. customThe residue is chromatographed through a silica gel column
  9. washeluted with an ether-methylene chloride (1:1) mixture

Sources & evidence

ORD record
ord-42c664d26547449497f084a40b37707d
Source dataset
uspto-grants-1980_04
Patent number
US04198420

Reaction notes

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