Water → HCID 22914782, compound

HRID 1534580Notes

Reaction equation

HRID 1534580 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)[CH2:4][CH2:3]1.[N:23]#CBr.O>C1C=CC=CC=1>[C:1]([N:2]1[CH2:3][CH2:4][C:5](=[C:8]2[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)[CH2:6][CH2:7]1)#[N:23]

Participants

5

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 22914794HCID 22914794, compound

Product 1

HCID 22914782HCID 22914782, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 400 mg (1.35 mmole) of 11-(1-methyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta [1,2-c]pyridine in 5.0 mL of benzene at room temperature and under an argon atmosphere was added dropwise a solution of 168 mg (1.59 mmole) of cyanogen bromide in 4 mL of benzene. After 30 min. the mixture was poured into water and extracted once with EtOAc. The organic layer was isolated, washed once with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via flash chromatography [21/2% MeOH in CH2Cl2 ] to give 150 mg (37%) of the title compound as a solid: m.p. 212°-214° C.

Workup

  1. extractionextracted once with EtOAc
  2. customThe organic layer was isolated
  3. washwashed once with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via flash chromatography [21/2% MeOH in CH2Cl2 ]

Sources & evidence

ORD record
ord-129b6c6fe9ed434eab7ddf176df0f261
Source dataset
uspto-grants-1992_02
Patent number
US05089496

Reaction notes

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