1-Heptanamine → HCID 10413322, compound

HRID 374050Notes

Reaction equation

HRID 374050 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=O)[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:44]([NH2:51])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]>C(Cl)Cl>[C:12]1([C:11]2[N:10]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([NH:51][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[O:28])[NH:8][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 81271-HeptanamineHCID 10868DicyclohexylcarbodiimideHCID 22916338HCID 22916338, compound

Product 1

HCID 10413322HCID 10413322, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part A. To a solution of 8-(4,5-diphenyl-1H-imidazol-2-ylthio)octanoic acid (8.44 g, 0.02 mol) in methylene chloride (100 mL) at 0° was added, portionwise as a solid, dicyclohexylcarbodiimide (4.12 g, 0.02 mol), and the reaction mixture was stirred at 0° for 30 minutes. To this reaction mixture was added, dropwise, heptylamine (2.96 mL, 2.3 g, 0.02 mol) and the reaction mixture was stirred at reflux for 72 hours. The reaction mixture was cooled, and the solids were filtered and washed with chloroform. The filtrate was concentrated under vacuum and the residue was chromatographed with a gradient of 7:3 to 1:1 hexane-ethyl acetate. The resulting solid was recrystallized from acetonitrile and triturated with hexane to give 8-(4,5-diphenyl-1H-imidazol-2-ylthio)-N-heptyloctanamide (3.28 g, 0.0067 mol) as a white solid, mp 119°-120°. 1H NMR (DMSO-d6) δ12.5(s,1H), 7.8-7.1(m,10H), 3.2-2.9(m,4H), 2.0(t,2H,J=7Hz), 1.75-1.0(m,21H), 1.0-0.8(m,3H).

Workup

  1. additionTo this reaction mixture was added
  2. temperatureat reflux for 72 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe solids were filtered
  5. washwashed with chloroform
  6. concentrationThe filtrate was concentrated under vacuum
  7. customthe residue was chromatographed with a gradient of 7:3 to 1:1 hexane-ethyl acetate
  8. customThe resulting solid was recrystallized from acetonitrile
  9. customtriturated with hexane

Sources & evidence

ORD record
ord-b4526a4ea2e74f84b17cdfb1da9922e9
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

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