Ethylmorpholine → HCID 86628722, compound

HRID 1071693Notes

Reaction equation

HRID 1071693 reaction equation
[C:1]([O:5][C:6]([CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:18](O)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1CCOCC1)C.Cl.[CH:30]([N:33]1[CH2:38][CH2:37][CH:36]([NH2:39])[CH2:35][CH2:34]1)([CH3:32])[CH3:31]>ClCCl>[CH:30]([N:33]1[CH2:38][CH2:37][CH:36]([NH:39][C:18]([C:10]2[N:9]([CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:17]3[C:12]([CH:11]=2)=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:19])[CH2:35][CH2:34]1)([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 7525EthylmorpholineHCID 21749024N-(tert-butoxycarbonylmethyl)-2-indolecarboxylic acidHCID 230334601-Isopropylpiperidin-4-amine hydrochloride

Product 1

HCID 86628722HCID 86628722, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.5 g 1-tert.-butoxycarbonylmethyl-1H-indole-2-carboxylic acid and 0.91 ml N-ethylmorpholine in 3 ml dichloromethane 0.6 g O-[(ethoxycarbonyl)cyanomethylenamino]-N,N,N′,N′-tetramethyluronium tetrafluoroborate were added and the mixture was stirred for 30 min at room temperature. 0.39 g 1-isopropyl-piperidin-4-ylamine hydrochloride were added to the mixture and the reaction mixture was further stirred for 1 hour. After removal of the solvent under reduced pressure the residue was partitioned between 15 ml water and 15 ml dichloromethane. The organic layer was washed with additional water and then dried over sodium sulphate. After filtration the solvent was removed under reduced pressure and a white solid was obtained. The residue was directly subjected to the subsequent reaction without further purification.

Workup

  1. stirringthe reaction mixture was further stirred for 1 hour
  2. customAfter removal of the solvent under reduced pressure the residue
  3. customwas partitioned between 15 ml water and 15 ml dichloromethane
  4. washThe organic layer was washed with additional water
  5. dry with materialdried over sodium sulphate
  6. filtrationAfter filtration the solvent
  7. customwas removed under reduced pressure
  8. customa white solid was obtained
  9. customThe residue was directly subjected to the subsequent reaction without further purification

Sources & evidence

ORD record
ord-37a5fa146fd443cfb9fd198d77a370cf
Source dataset
uspto-grants-2005_06
Patent number
US06906084B2

Reaction notes

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