Hydrochloric Acid → HCID 71079564, compound

HRID 337208Notes

Reaction equation

HRID 337208 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([C:26]([CH:28]2[CH2:30][CH2:29]2)=[O:27])[CH2:21][CH2:20]3)(=[O:16])=[O:15])[CH2:10][CH2:9]1)(C)(C)C.Cl>O1CCOCC1>[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([C:26]([CH:28]2[CH2:29][CH2:30]2)=[O:27])[CH2:21][CH2:20]3)(=[O:16])=[O:15])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71079542HCID 71079542, compound

Product 1

HCID 71079564HCID 71079564, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[1-(1-Cyclopropanecarbonyl-2,3-dihydro-1H-indole-5-sulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.36 g, 0.8 mmol) was suspended in a 4M solution of HCl in Dioxane (10 ml). The resulting suspension was stirred at room temperature for 3 hours. After this time the solution was concentrated under vacuum, then azeotroped with methanol and suspended in diethyl ether. The resulting solid precipitate was then collected by filtration, washed with diethyl ether and dried under vacuum to afford the title compound (0.09 g, 32% yield) as a white solid. Tr=1.36 min, m/z (ES+) (M+H)+ 350.

Workup

  1. concentrationAfter this time the solution was concentrated under vacuum
  2. customazeotroped with methanol
  3. filtrationThe resulting solid precipitate was then collected by filtration
  4. washwashed with diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-aed62616803741fda3095d724cccbd4b
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

Loading…