Allyl bromide → N-(4-chlorophenyl)-1-(2-propenyl)-4-piperidinamine

HRID 2049365Notes

Reaction equation

HRID 2049365 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:23][CH:24]=[CH2:25]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:25][CH:24]=[CH2:23])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 7183033N-(4-chlorophenyl)piperidin-4-amine

Product 1

HCID 23339007N-(4-chlorophenyl)-1-(2-propenyl)-4-piperidinamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred mixture of 15 parts of N-(4-chlorophenyl)4-piperidinamine, 12 parts of N,N-diethylethanamine in 130 parts of benzene is added dropwise a solution of 10.3 parts of 3-bromo-1-propene in 70 parts of benzene. Upon completion, the whole is stirred first for 20h.30 at room temperature and futher for 40 minutes at reflux. The reaction mixture is cooled, filtered and the filtrate is evaporated. The residue is taken up in 1,1'-oxybisethane and treated with activated charcoal. The latter is filtered off and the 1,1'-oxybisethane is evaporated again, yielding 2.9 parts of N-(4-chlorophenyl)-1-(2-propenyl)-4-piperidinamine; mp. 90° C.

Workup

  1. temperaturefuther for 40 minutes at reflux
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. customthe filtrate is evaporated
  5. additiontreated with activated charcoal
  6. filtrationThe latter is filtered off
  7. customthe 1,1'-oxybisethane is evaporated again

Sources & evidence

ORD record
ord-32188ee617444be6b9a00fef6edac302
Source dataset
uspto-grants-1980_04
Patent number
US04197304

Reaction notes

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