Methylamine → 6-(4-Phenylbutoxy)hexan-1-amine

HRID 275418Notes

Reaction equation

HRID 275418 reaction equation
C1(CCCCOCCCCCCBr)C=CC=CC=1.C1(=O)NC(=O)C2=CC=CC=C12.[K].[C:31]1([CH2:37][CH2:38][CH2:39][CH2:40][O:41][C:42]2[CH:43]=[CH:44][CH:45]=[C:46]3[C:51](=O)[N:50](CCCCCC)C(=O)C=23)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CN>CC(C)=O.ClCCl>[C:31]1([CH2:37][CH2:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:51][NH2:50])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 110124391-[4-[(6-Bromohexyl)oxy]butyl]benzeneHCID 200881216-(4-phenyl-butoxy)-N-hexyl-phthalimideHCID 24194345Phthalimide potassium salt

Product 1

HCID 109669026-(4-Phenylbutoxy)hexan-1-amine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 46.6 g (0.15 mol) of 6-(4-phenylbutoxy)-hexyl-bromide and 27.6 g (0.15 mol) of potassium phthalimide in 400 ml of acetone is refluxed for 70 hours. After cooling, the potassium bromide precipitated is removed by suction filtering and the solvent is distilled off in vacuo. The oily residue thus obtained, consisting of crude 6-(4-phenyl-butoxy)-N-hexyl-phthalimide, is stirred into 300 ml of dichloromethane and 300 ml of 40% methylamine solution overnight. The organic phase is separated off and the aqueous phase is extracted twice more with dichloromethane. The combined organic phases are dried over sodium sulphate and evaporated down in vacuo. The oily residue is dissolved in ether, the solids precipitated are filtered off and the filtrate is evaporated to dryness. The colorless oil remaining is distilled. Bp0.2 =143°-145° C.

Workup

  1. temperatureAfter cooling
  2. customthe potassium bromide precipitated
  3. customis removed by suction
  4. filtrationfiltering
  5. distillationthe solvent is distilled off in vacuo
  6. customThe oily residue thus obtained
  7. customThe organic phase is separated off
  8. extractionthe aqueous phase is extracted twice more with dichloromethane
  9. dry with materialThe combined organic phases are dried over sodium sulphate
  10. customevaporated down in vacuo
  11. dissolutionThe oily residue is dissolved in ether
  12. customthe solids precipitated
  13. filtrationare filtered off
  14. customthe filtrate is evaporated to dryness
  15. distillationThe colorless oil remaining is distilled
  16. customBp0.2 =143°-145° C.

Sources & evidence

ORD record
ord-b6e1e48aaa1f4a82b917aa9282dada9f
Source dataset
uspto-grants-1995_02
Patent number
US05393774

Reaction notes

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