Dichloromethane → HCID 13306782, compound

HRID 464047Notes

Reaction equation

HRID 464047 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][C:14](CC)([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:30]#[C:31]Br.[Cl:33]CCl>>[ClH:33].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:17]([N:18]3[CH:22]=[CH:21][CH:20]=[CH:19]3)[C:31]#[N:30])[CH2:15][CH2:16]2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 20263914HCID 20263914, compound

Product 1

HCID 13306782HCID 13306782, compoundYield 58%

Procedure

To a solution of 1-[2-(4-methoxyphenyl)ethyl]-4-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%) of 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-ffdda5ae943b424290423675d2c20ff5
Source dataset
uspto-grants-1985_10
Patent number
US04546105

Reaction notes

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