Cyanogen Bromide → {2-[1-(4-Methoxyphenyl)cyclopentyl]ethyl}methylcyanamide

HRID 1679175Notes

Reaction equation

HRID 1679175 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][C:5]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1.[N:19]#CBr>C(Cl)(Cl)Cl>[C:18]([N:2]([CH2:3][CH2:4][C:5]1([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[CH2:6][CH2:7][CH2:8][CH2:9]1)[CH3:1])#[N:19]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 20364029HCID 20364029, compound

Product 1

HCID 53992609{2-[1-(4-Methoxyphenyl)cyclopentyl]ethyl}methylcyanamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

By following the manipulative procedure outlined above in Example 12, a solution of 5.43 g of 1-(2-dimethylaminoethyl)-1-(4-methoxyphenyl)cyclopentane (the free base of Example 46) in chloroform is added to a stirred solution of 2.57 g of cyanogen bromide in chloroform to give an oil. The oil is dissolved in chlorofrom, subjected to column chromatography with a silica gel column and eluted with ether to produce an orange oil of 1-(N-cyano-N-methylaminoethyl)-1-(4-methoxyphenyl)cyclopentane.

Workup

  1. customto give an oil
  2. dissolutionThe oil is dissolved in chlorofrom
  3. washeluted with ether

Sources & evidence

ORD record
ord-631257f9d82d4b87accfa6817a16f9d0
Source dataset
uspto-grants-1978_03
Patent number
US04079141

Reaction notes

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