Dicyclohexylcarbodiimide → 5,6,6a,7,8,9,10,10a-Octahydro-2-(4-morpholinobutyryloxy)-10-hydroxymethyl-6,6-dimethyl-3-(1-methyl-4-phenylbutyl)benzo[c]quinoline Hydrochloride

HRID 1706258Notes

Reaction equation

HRID 1706258 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12]([CH3:22])[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:8][C:7]([CH3:24])([CH3:23])[CH:6]1[CH2:25][CH2:26][CH2:27][CH:28]([CH2:29][OH:30])[CH:5]21.[ClH:31].[O:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][CH2:40][C:41](O)=[O:42])[CH2:34][CH2:33]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[ClH:31].[O:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][CH2:40][C:41]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[CH:12]([CH3:22])[CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:8][C:7]([CH3:23])([CH3:24])[CH:6]2[CH2:25][CH2:26][CH2:27][CH:28]([CH2:29][OH:30])[CH:5]32)=[O:42])[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 127337464-Morpholin-4-Yl-Butyric Acid HydrochlorideHCID 203374355,6,6a,7,8,9,10,10a-Octahydro-2-hydroxy-10-hydroxymethyl-6,6-dimethyl-3-(1-methyl-4-phenylbutyl)benzo[c]quinoline

Product 1

HCID 203374685,6,6a,7,8,9,10,10a-Octahydro-2-(4-morpholinobutyryloxy)-10-hydroxymethyl-6,6-dimethyl-3-(1-methyl-4-phenylbutyl)benzo[c]quinoline Hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 25° C. solution of 5,6,6a,7,8,9,10,10a-octahydro-2-hydroxy-10-hydroxymethyl-6,6-dimethyl-3-(1-methyl-4-phenylbutyl)benzo[c]quinoline (626 mg., 1.5 mmole) in dry methylene chloride (25 ml.) is added 4-morpholinobutyric acid hydrochloride (0.315 g., 1.5 mmole) and the mixture stirred at room temperature under a nitrogen atmosphere. A 0.1 M solution of dicyclohexylcarbodiimide in methylene chloride (12.5 ml., 1.5 mmole) is added dropwise and the mixture stirred for 6 hours. It is then cooled in ice, filtered and evaporated to give the title product which is purified as the free base by column chromatography on silica gel.

Workup

  1. stirringthe mixture stirred for 6 hours
  2. temperatureIt is then cooled in ice
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-ef7c6c5344d84e4695af75ccaa423ec7
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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