Ammonium Chloride → HCID 19747289, compound

HRID 484307Notes

Reaction equation

HRID 484307 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5](Cl)[CH2:4][CH2:3]1.[Mg].[C:10]([C:12]1[CH:13]=[CH:14][C:15]2[C:25](=[O:26])[C:20]3[NH:21][CH2:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][C:16]=2[CH:27]=1)#[N:11].[Cl-].[NH4+]>O1CCCC1>[C:10]([C:12]1[CH:13]=[CH:14][C:15]2[C:25]([CH:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)([OH:26])[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH2:18][CH2:17][C:16]=2[CH:27]=1)#[N:11]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 19747241HCID 19747241, compound

Product 1

HCID 19747289HCID 19747289, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a tetrahydrofuran (THF) solution of a Grignard reagent prepared from 6.7 g of N-methyl-4-chloropiperidine and 1.2 g of magnesium, 4.68 g of 8-cyano5,6-dihydro-1H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (the compound prepared in Referential Example 1) were added under ice cooling. After the resultant mixture was stirred for 3 hours at room temperature, a saturated aqueous solution of ammonium chloride was added, followed by stirring for 15 minutes. The reaction mixture was then extracted with chloroform. The Extract was dried over anhydrous Na2SO4 and then filtered. The filtrate so obtained was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column and, from relevant fractions eluted with chloroform:methanol (50:1), 3.1 g of 8-cyano-6,11-dihydro-11-(1-methyl-4-piperidyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol were obtained (yield: 47%).

Workup

  1. customprepared in Referential Example 1)
  2. additionwere added under ice cooling
  3. extractionThe reaction mixture was then extracted with chloroform
  4. dry with materialThe Extract was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customThe filtrate so obtained
  7. concentrationwas concentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column and, from relevant fractions
  9. washeluted with chloroform:methanol (50:1)

Sources & evidence

ORD record
ord-5d637f8a96ff427689f211e33eaf18f2
Source dataset
uspto-grants-1993_07
Patent number
US05231101

Reaction notes

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