4-Methylmorpholine → [3-(Dimethylamino)-1-piperidinyl]-1H-indol-3-ylmethanone

HRID 1032700Notes

Reaction equation

HRID 1032700 reaction equation
Cl.Cl.[CH3:3][N:4]([CH3:11])[CH:5]1[CH2:10][CH2:9][CH2:8][NH:7][CH2:6]1.CN1CCOCC1.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([C:28](O)=[O:29])=[CH:20]1.C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)/C=C\C(O)=O>C(O)(C)C.CCOCC.ClCCl>[CH3:3][N:4]([CH3:11])[CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:28]([C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:19][CH:20]=2)=[O:29])[CH2:6]1

Participants

9

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 69867Indole-3-Carboxylic AcidHCID 444266Maleic AcidHCID 14459855N,N-Dimethylpiperidin-3-amine--hydrogen chloride (1/2)

Product 1

HCID 9903567[3-(Dimethylamino)-1-piperidinyl]-1H-indol-3-ylmethanone

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-dimethylaminopiperidine dihydrochloride (1.8 g, 0.01 mol), N-methylmorpholine (2.5 g) and dichloromethane (50 ml) was stirred at ambient temperature for 1.5 h. Indole-3-carboxylic acid (1.92 g, 0.012 mol) was added, followed by dicyclohexylcarbodiimide (2.5 g) and the mixture stirred for 24 h. The mixture was filtered, the filtrate was washed thrice with 1M hydrochloric acid, the acid washings were combined, basified with ammonia and extracted with chloroform. The chloroform extract was dried and evaporated to yield the product base 1.6 g. The base was dissolved in isopropyl alcohol (20ml), acidified with maleic acid (0.72 g, 5% excess) and diluted with ether (10 ml). On standing the maleate salt crystallised and was collected by filtration, 1.04 g, mp 139-141.

Workup

  1. stirringthe mixture stirred for 24 h
  2. filtrationThe mixture was filtered
  3. washthe filtrate was washed thrice with 1M hydrochloric acid
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. customwas dried
  7. customevaporated
  8. customto yield the product base 1.6 g
  9. customcrystallised
  10. filtrationwas collected by filtration, 1.04 g, mp 139-141

Sources & evidence

ORD record
ord-fbf17b3555e84a708d574706ac6ea66c
Source dataset
uspto-grants-1990_09
Patent number
US04959375

Reaction notes

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