Triethylamine → N-[1-(benzyl)-2-(phenyl)-ethyl]-cis-2-Octyl-cyclopropanoctanamide

HRID 1413132Notes

Reaction equation

HRID 1413132 reaction equation
[CH2:1]([C@H:9]1[CH2:11][C@H:10]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(CC)CC)C.C(OC(Cl)=O)C.[CH2:35]([CH:42]([NH2:50])[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl>[CH2:43]([CH:42]([NH:50][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C@@H:10]1[CH2:11][C@@H:9]1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 779601,3-Diphenyl-2-aminopropaneHCID 11426463cis-8-(2-Octylcyclopropyl) octanoic acid

Product 1

HCID 13131904N-[1-(benzyl)-2-(phenyl)-ethyl]-cis-2-Octyl-cyclopropanoctanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 2.0 g (cis)-2-octylcyclopropanoctanoic acid in 70 ml methylene chloride at -20° is added first 0.707 g triethylamine and then dropwise 0.732 g ethylchloroformate. The reaction mixture is then allowed to come to room temperature and stirred for 1 hours. Then 1.5 g of 1-benzyl-2-(phenyl)ethylamine is added, and the reaction mixture stirred for 16 hours. The reaction mixture is then extracted a few times with 2 N hydrochloric acid, then with 2 N aq. sodium hydroxide sol. and washed several times with saturated aq. sodium chloride. The organic phase is then dried over anh. sodium sulphate filtered and evaporated i.v. to dryness to obtain a residue, which upon crystallization from pentane yields the title product (m.p. 40°-45°).

Workup

  1. customto come to room temperature
  2. stirringthe reaction mixture stirred for 16 hours
  3. extractionThe reaction mixture is then extracted a few times with 2 N hydrochloric acid
  4. washwith 2 N aq. sodium hydroxide sol. and washed several times with saturated aq. sodium chloride
  5. dry with materialThe organic phase is then dried over anh. sodium sulphate
  6. filtrationfiltered
  7. customevaporated i.v
  8. customto dryness to obtain a residue, which
  9. customupon crystallization from pentane

Sources & evidence

ORD record
ord-b3e450c85cb64983be9d4080d00244ec
Source dataset
uspto-grants-1981_02
Patent number
US04248893

Reaction notes

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