N-Propargylbenzylamine → HCID 131716820, compound

HRID 1084336Notes

Reaction equation

HRID 1084336 reaction equation
Br[C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[CH2:16]([NH:23][CH2:24][C:25]#[CH:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[CH2:16]([NH:23][CH2:24][C:25]#[C:26][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 99277N-PropargylbenzylamineHCID 14256374HCID 14256374, compound

Product 1

HCID 131716820HCID 131716820, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 g of dimethyl 5-bromodicarboxylate (from Example 3) and 1.25 g of N-benzylpropargylamine are dissolved in methylene chloride in a flask flushed with argon, and 3.4 ml of triethylamine are added dropwise. The mixture is stirred at room temperature for 15 minutes, 25 mg of ((C6H5)3P)2PdCl2 and 4 mg of CuI are added and the mixture is boiled under reflux for 36 hours. After cooling, the mixture is diluted with methylene chloride and washed with water and sodium chloride solution and the combined organic phases are dried over potassium carbonate. After evaporation, 1.25 g of a dark oil which is hydrogenated without purification (Example 18) remain.

Workup

  1. customflushed with argon, and 3.4 ml of triethylamine
  2. additionare added dropwise
  3. addition25 mg of ((C6H5)3P)2PdCl2 and 4 mg of CuI are added
  4. temperatureunder reflux for 36 hours
  5. temperatureAfter cooling
  6. additionthe mixture is diluted with methylene chloride
  7. washwashed with water and sodium chloride solution
  8. dry with materialthe combined organic phases are dried over potassium carbonate
  9. customAfter evaporation, 1.25 g of a dark oil which
  10. customis hydrogenated without purification (Example 18)

Sources & evidence

ORD record
ord-12a4789e07bd4be997cbc9e9ce46b73d
Source dataset
uspto-grants-1991_04
Patent number
US05004748

Reaction notes

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