Dicyclohexylcarbodiimide → {[5,5-Dimethyl-8-(1,2-dimethylheptyl)-10-(4-piperidinobutyryloxy)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridin-2-yl]acetyl}urea hydrochloride

HRID 427100Notes

Reaction equation

HRID 427100 reaction equation
[OH:1][C:2]1[C:7]2[C:8]3[CH2:9][N:10]([CH2:18][C:19]([NH:21][C:22]([NH2:24])=[O:23])=[O:20])[CH2:11][CH2:12][C:13]=3[C:14]([CH3:17])([CH3:16])[O:15][C:6]=2[CH:5]=[C:4]([CH:25]([CH3:33])[CH:26]([CH3:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:3]=1.[ClH:34].[N:35]1([CH2:41][CH2:42][CH2:43][C:44](O)=[O:45])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[ClH:34].[CH3:17][C:14]1([CH3:16])[C:13]2[CH2:12][CH2:11][N:10]([CH2:18][C:19]([NH:21][C:22]([NH2:24])=[O:23])=[O:20])[CH2:9][C:8]=2[C:7]2[C:2]([O:1][C:44](=[O:45])[CH2:43][CH2:42][CH2:41][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:3][C:4]([CH:25]([CH3:33])[CH:26]([CH3:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:5][C:6]=2[O:15]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 131720814-(Piperidin-1-yl)butanoic acid hydrochlorideHCID 20388001{[10-Hydroxy-5,5-dimethyl-8-(1,2-dimethylheptyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridin-2-yl]acetyl}urea

Product 1

HCID 131711650{[5,5-Dimethyl-8-(1,2-dimethylheptyl)-10-(4-piperidinobutyryloxy)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridin-2-yl]acetyl}urea hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
6 °C

Procedure

A mixture of 1.14 g. (0.0025 mole) of {[10-hydroxy-5,5-dimethyl-8-(1,2-dimethylheptyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridin-2-yl]acetyl}urea, 0.52 g. (0.0025 mole) of 4-piperidinobutyric acid hydrochloride, 0.54 g. (0.0026 mole) of dicyclohexylcarbodiimide, and 170 ml. of dried methylene chloride was stirred at room temperature for 26 hours. The reaction mixture was cooled at approximately 6° C. overnight and was filtered to remove dicyclohexylurea. The filtrate was evaporated in vacuo and the residue was dissolved in 3 ml. of methylene chloride and 12.5 ml. of cyclohexane. After standing overnight in the cold room (approximately 6° C.), the solid was filtered and recrystallized from methylene chloride-ether, giving 1.1 g. of the product, m.p. 167°-170°.

Workup

  1. additionA mixture of 1.14 g
  2. filtrationwas filtered
  3. customto remove dicyclohexylurea
  4. customThe filtrate was evaporated in vacuo
  5. dissolutionthe residue was dissolved in 3 ml
  6. filtrationthe solid was filtered
  7. customrecrystallized from methylene chloride-ether
  8. customgiving 1.1 g

Sources & evidence

ORD record
ord-39ffb2ba07a34335afe5558f04657ec4
Source dataset
uspto-grants-1979_10
Patent number
US04172943

Reaction notes

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