Laurolactam → n-(cis-2-Phenyl-cyclopentyl) azacyclotridecan-2-imine-hydrochloride

HRID 461043Notes

Reaction equation

HRID 461043 reaction equation
[C:1]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2]1.P(Cl)(Cl)([Cl:17])=O.Cl.[C:21]1([C@H:27]2[CH2:31][CH2:30][CH2:29][C@H:28]2[NH2:32])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1C=CC=CC=1>[ClH:17].[C:21]1([C@H:27]2[CH2:31][CH2:30][CH2:29][C@H:28]2[N:32]=[C:1]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 13690LaurolactamHCID 24813Phosphorus oxychlorideHCID 70051154rac-(1R,2R)-2-phenylcyclopentan-1-amine hydrochloride

Product 1

HCID 136349517n-(cis-2-Phenyl-cyclopentyl) azacyclotridecan-2-imine-hydrochloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 21.7 g of 2-azacyclotridecanone in 200 ml of dry benzene is added dropwise 15.3 g of phosphorus oxychloride. The mixture is stirred at room temperature for 4 hours after which 19.8 g of cis-2-phenylcyclopentylamine hydrochloride is added. The reaction mixture is stirred at room temperature for 2 hours and refluxed for 24 hours. The resulting homogeneous solution is washed with 2N NaOH, 2N HCl and saturated NaCl solution, dried over sodium sulfate and the solvent evaporated. The resulting oily product crystallized from acetone is recrystallized from methanol-acetone to give the desired product, M.P. 156°-159° C.

Workup

  1. additionis added
  2. temperaturerefluxed for 24 hours
  3. washThe resulting homogeneous solution is washed with 2N NaOH, 2N HCl and saturated NaCl solution
  4. dry with materialdried over sodium sulfate
  5. customthe solvent evaporated
  6. customThe resulting oily product crystallized from acetone
  7. customis recrystallized from methanol-acetone

Sources & evidence

ORD record
ord-daa5857888b34c6cab0c4e6ecf65a1c4
Source dataset
uspto-grants-1977_12
Patent number
US04061746

Reaction notes

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