Dichloromethane → HCID 13306782, compound

HRID 1262581Notes

Reaction equation

HRID 1262581 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([NH:17][N:18]3[CH:22]=[CH:21][CH:20]=[CH:19]3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[N:28]#[C:29]Br.[Cl:31]CCl>>[ClH:31].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]([N:18]3[CH:22]=[CH:21][CH:20]=[CH:19]3)[C:29]#[N:28])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 20263895HCID 20263895, compound

Product 1

HCID 13306782HCID 13306782, compoundYield 58%

Procedure

To a solution of 1-[2-(4-methoxyphenyl)ethyl]-4-(1H-pyrrol-1-yl)aminopiperidine of Example 12a (4 g, 13.4 mmole) in 150 ml dichloromethane containing sodium bicarbonate (3.4 g, 40 mmole) was added a solution of cyanogen bromide (1.6 g, 14.7 mmole) in 25 ml dichloromethane. After stirring twenty hours at ambient temperature, the reaction mixture was evaporated, stirred with water and extracted with ether. The organic extract was washed with water and saturated NaCl and was dried (anhydrous MgSO4), filtered and evaporated to 5 g of an oil. The oil was converted to the hydrochloride salt as in Example 2 and was recrystallized from isopropanol-ether to give 2.8 g (58%) N-{1-[2-(4-methoxyphenyl)ethyl]piperidin-4-yl}-N-(1H-pyrrol-1-yl)cyanamide hydrochloride, d 227°-229° C.

Workup

  1. customthe reaction mixture was evaporated
  2. stirringstirred with water
  3. extractionextracted with ether
  4. extractionThe organic extract
  5. washwas washed with water and saturated NaCl
  6. dry with materialwas dried (anhydrous MgSO4)
  7. filtrationfiltered
  8. customevaporated to 5 g of an oil
  9. customwas recrystallized from isopropanol-ether

Sources & evidence

ORD record
ord-7930693325dc4f0c813c2af4d06b3f44
Source dataset
uspto-grants-1984_06
Patent number
US04452803

Reaction notes

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