Triethylamine → 1-[4-(16-Bromohexadecylamino)benzoyl]pyrrolidine

HRID 1106167Notes

Reaction equation

HRID 1106167 reaction equation
C([N:11]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][Br:28])(OCC1C=CC=CC=1)=O.[CH2:38]([N:40](CC)[CH2:41][CH3:42])[CH3:39].N1CCCC1>CCOCC>[Br:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:29]1[CH:30]=[CH:31][C:32]([C:33]([N:40]2[CH2:41][CH2:42][CH2:39][CH2:38]2)=[O:34])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 20482544N-Carbobenzyloxy-4-(16-bromohexadecylamino)benzoyl chloride

Product 1

HCID 130254121-[4-(16-Bromohexadecylamino)benzoyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 6.0 g. of 4-[N-carbobenzyloxy-N-(16-bromohexadecyl)amino]benzoyl chloride and 1.2 g. triethylamine in 100 ml. warm ether is treated with 1.1 g. of pyrrolidine. After 1 hour at reflux, the precipitate is filtered off and washed with warm ether. After evaporation in dryness, the intermediate is dissolved in 50 ml. 30% hydrobromic/acetic acid and warmed at 50° for 2 hours. The solvents are evaporated and the product is partitioned between methylene chloride and water. The layers are separated and the methylene chloride is evaporated. The residue is crystallized from acetone to yield colorless crystals.

Workup

  1. temperatureAfter 1 hour at reflux
  2. filtrationthe precipitate is filtered off
  3. washwashed with warm ether
  4. customAfter evaporation in dryness
  5. dissolutionthe intermediate is dissolved in 50 ml
  6. temperature30% hydrobromic/acetic acid and warmed at 50° for 2 hours
  7. customThe solvents are evaporated
  8. customthe product is partitioned between methylene chloride and water
  9. customThe layers are separated
  10. customthe methylene chloride is evaporated
  11. customThe residue is crystallized from acetone
  12. customto yield colorless crystals

Sources & evidence

ORD record
ord-0cd8674b68f14079854db1faf0c39ac9
Source dataset
uspto-grants-1982_01
Patent number
US04311846

Reaction notes

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