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

HRID 1679647

Reaction equation

HRID 1679647 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].[CH3:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][N:36]1[CH2:41][CH2:42][CH2:43][C:44](O)=[O:45].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.C(OCC)C>[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][N:36]3[CH2:37][CH2:38][CH2:39][CH2:40][CH:35]3[CH3:34])=[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

6

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 705657274-(2-Methylpiperidin-1-yl)butanoic acid hydrochloride

Product 1

HCID 888085825,5-Dimethyl-10-[4-(2-methylpiperidino)butyryloxy]-8-(4-fluorophenyl-1-methylbutyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[3,4-d] pyridine hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of equimolar quantities 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, γ-(2-methylpiperidino)butyric acid hydrochloride and dicyclohexylcarbodiimide in methylene chloride are stirred at room temperature for 16 hours. The reaction mixture is cooled and the solid removed by suction filtration. The methylene chloride is evaporated to give a residue which is dissolved in methylene chloride and diethyl ether. After removing the resulting crude product, the solvents are evaporated and the gummy resin is dried, triturated with diethyl ether, and dried to yield the desired product.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe solid removed by suction filtration
  3. customThe methylene chloride is evaporated
  4. customto give a residue which
  5. customAfter removing the resulting crude product
  6. customthe solvents are evaporated
  7. customthe gummy resin is dried
  8. customtriturated with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-1bc8620444044b39a39e3cbfe07a0178
Source dataset
uspto-grants-1978_03
Patent number
US04081449

Linked notes

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