Dicyclohexylcarbodiimide → 5,5-Dimethyl-8-(1,2-dimethylheptyl)-10-(4-piperidinobutyrylamino)-5H-[1]benzopyrano [4,3-c]pyridine hydrochloride

HRID 1763296Notes

Reaction equation

HRID 1763296 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]3[CH:9]=[N:10][CH:11]=[CH:12][C:13]=3[C:14]([CH3:17])([CH3:16])[O:15][C:6]=2[CH:5]=[C:4]([CH:18]([CH3:26])[CH:19]([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:3]=1.[ClH:27].[N:28]1([CH2:34][CH2:35][CH2:36][C:37](O)=[O:38])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[ClH:27].[CH3:17][C:14]1([CH3:16])[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]2[C:2]([NH:1][C:37](=[O:38])[CH2:36][CH2:35][CH2:34][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:3][C:4]([CH:18]([CH3:26])[CH:19]([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:5][C:6]=2[O:15]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 131720814-(Piperidin-1-yl)butanoic acid hydrochlorideHCID 2030973410-Amino-5,5-dimethyl-8-(1,2-dimethylheptyl)-5H-[1]benzopyrano[4,3-c]pyridine

Product 1

HCID 1317112225,5-Dimethyl-8-(1,2-dimethylheptyl)-10-(4-piperidinobutyrylamino)-5H-[1]benzopyrano [4,3-c]pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.87 g. (2.47 mmole) of 10-amino-5,5-dimethyl-8-(1,2-dimethylheptyl)-5H-[1]benzopyrano[4,3-c]-pyridine, 0.51 g. (2.47 mmole) of 4-piperidinobutyric acid hydrochloride, 0.56 g. (2.72 mmole) of dicyclohexylcarbodiimide, and 50 ml. of dry methylene chloride was stirred at room temperature for 72 hours. The mixture was cooled and filtered and the filtrate concentrated to a residue which was recrystallized from methylene chloride-ether, m.p. 185-186°.

Workup

  1. additionA mixture of 0.87 g
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated to a residue which
  5. customwas recrystallized from methylene chloride-ether, m.p. 185-186°

Sources & evidence

ORD record
ord-115b97623b824b87960db21a7c5ed223
Source dataset
uspto-grants-1978_09
Patent number
US04111942

Reaction notes

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