Cyanogen Bromide → HCID 86733956, compound

HRID 1576269Notes

Reaction equation

HRID 1576269 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][C:10]3[C:15]([C:16]4([CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3.[N:23]#CBr>C(Cl)Cl>[C:22]([N:19]1[CH2:20][CH2:21][C:16]2([C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[CH2:9][C:10]3[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:17][CH2:18]1)#[N:23]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 86733957HCID 86733957, compound

Product 1

HCID 86733956HCID 86733956, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxy-1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine (12.6 g.) and cyanogen bromide (5.6 g.) in methylene chloride (250 ml.) are stirred at room temperature for 18 hours. The reaction mixture is evaporated to dryness, and the residue is taken up in chloroform, the solution washed with water and with brine, dried (MgSO4), and evaporated to give a brown oil which is chromatographed rapidly on silica gel. Elution with ethyl acetate affords pure 1'-cyano-4-methoxy-9,10-dihydroanthracene-9-spiro-4'-piperidine as an oil, characterised by the peak at 2200 cm-1 (C≡N stretching) in its infra-red spectrum.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. washthe solution washed with water and with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a brown oil which
  6. customis chromatographed rapidly on silica gel
  7. washElution with ethyl acetate

Sources & evidence

ORD record
ord-408bcd9293a546f9878f02442e9eba1f
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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