Dicyclohexylcarbodiimide → 5,5-Dimethyl-10-[5-(piperidino)valeryloxy]-8-(4-fluorophenyl-1-methylbutyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[3,4-d]pyridine hydrochloride

HRID 2398864Notes

Reaction equation

HRID 2398864 reaction equation
[CH3:1][C:2]1([CH3:32])[C:24]2[CH2:25][CH2:26][N:27]([CH2:29][C:30]#[CH:31])[CH2:28][C:23]=2[C:5]2[C:6]([OH:22])=[CH:7][C:8]([C:10]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)([CH3:14])[CH2:11][CH2:12][CH3:13])=[CH:9][C:4]=2[O:3]1.[ClH:33].[N:34]1([CH2:40][CH2:41][CH2:42][CH2:43][C:44](O)=[O:45])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[ClH:33].[CH3:32][C:2]1([CH3:1])[C:24]2[CH2:25][CH2:26][N:27]([CH2:29][C:30]#[CH:31])[CH2:28][C:23]=2[C:5]2[C:6]([O:22][C:44](=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:7][C:8]([C:10]([C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)([CH3:14])[CH2:11][CH2:12][CH3:13])=[CH:9][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 538194395,5dimethyl-10-hydroxy-8-(4-fluorophenyl-1-methylbutyl)-2(2-propynyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[3,4-d]pyridineHCID 545927615-(Piperidin-1-yl)pentanoic acid hydrochloride

Product 1

HCID 888088515,5-Dimethyl-10-[5-(piperidino)valeryloxy]-8-(4-fluorophenyl-1-methylbutyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[3,4-d]pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.4 g. (6.06 mm.) of 5,5-dimethyl-10-hydroxy-8-(4-fluorophenyl-1-methylbutyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[3,4-d]pyridine, 1.35 g. (6.06 mm.) of δ-piperidinovaleric acid hydrochloride and 1.30 g. (6.30 mm.) of dicyclohexylcarbodiimide in 100 ml. of methylene chloride are stirred at room temperature for 5 hours. The reaction mixture is cooled overnight in the refrigerator and the by-product of dicyclohexylurea removed by suction filtration. The mother liquor is evaporated and the residue dissolved in a mixture of methylene chloride/cyclohexane and allowed to stand in the cold for 2 hours. Gravity filtration separates the small amount of solid which appears, and the solvents are removed using a rotary evaporator. Crystallization from methylene chloride/diethyl ether yields the desired product.

Workup

  1. additionA mixture of 2.4 g
  2. temperatureThe reaction mixture is cooled overnight in the refrigerator
  3. customthe by-product of dicyclohexylurea removed by suction filtration
  4. customThe mother liquor is evaporated
  5. dissolutionthe residue dissolved in a mixture of methylene chloride/cyclohexane
  6. customcold for 2 hours
  7. filtrationGravity filtration
  8. customthe solvents are removed
  9. customa rotary evaporator
  10. customCrystallization from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-1fc2e70498a64f86871521211d90028c
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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