Cyclopropylamine → 60514-83-2

HRID 1076781Notes

Reaction equation

HRID 1076781 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][Cl:14])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17]1([NH2:20])[CH2:19][CH2:18]1>>[ClH:14].[CH:17]1([NH:20][CH2:13][C:12]2[CH:15]=[CH:16][C:9]([C:8]#[C:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:10][CH:11]=2)[CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 69828Cyclopropylamine2×HCID 21417396HCID 21417396, compound

Product 1

HCID 2153833260514-83-2

Procedure

A solution of 0.9 g. (4 mmole) of 4-(phenylethynyl)-benzyl chloride in 3 ml. of cyclopropylamine is heated to refluxing for 2 hours and then is allowed to stand at room temperature for several days. Another 1 ml. of cyclopropylamine is added and the solution is heated to refluxing for 4 hours. After evaporation of the excess cyclopropylamine, the residue is triturated with ether and the precipitate removed by filtration. The ethereal filtrate is evaporated and the residual oil dissolved in benzene. This solution is shaken with 10 ml. of 3N hydrochloric acid. The white crystalline hydrochloride salt of the product precipitates. It is collected and recrystallized twice from absolute methanol to give N-cyclopropyl-4-(phenylethynyl)-benzylamine hydrochloride, m.p. 210°-212°C. dec.

Workup

  1. temperatureto refluxing for 2 hours
  2. waitto stand at room temperature for several days
  3. temperaturethe solution is heated
  4. temperatureto refluxing for 4 hours
  5. customAfter evaporation of the excess cyclopropylamine
  6. customthe residue is triturated with ether
  7. customthe precipitate removed by filtration
  8. customThe ethereal filtrate is evaporated
  9. dissolutionthe residual oil dissolved in benzene
  10. customThe white crystalline hydrochloride salt of the product precipitates
  11. customIt is collected
  12. customrecrystallized twice from absolute methanol

Sources & evidence

ORD record
ord-bef2521992234e1b8c9a29c148c31804
Source dataset
uspto-grants-1976_05
Patent number
US03957871

Reaction notes

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