Hydrochloric Acid → (+/-)-trans-N-[(5-Chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride

HRID 459473Notes

Reaction equation

HRID 459473 reaction equation
C(O)C.Cl.C(OC([NH:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[NH:19][C:20]([C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][C:27]([Cl:31])=[CH:26][CH:25]=2)=[O:21])=O)(C)(C)C>ClCCl>[ClH:31].[Cl:31][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22]([C:20]([NH:19][C@@H:14]1[CH2:15][CH2:16][CH2:17][CH2:18][C@H:13]1[NH2:12])=[O:21])=[CH:30]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 68910309(+/-)-trans-N1-(tert-Butoxycarbonyl)-N2-[(5-chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamine

Product 1

HCID 18442870(+/-)-trans-N-[(5-Chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochlorideYield 198.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A saturated ethanol solution (100 ml) of hydrochloric acid was added to a solution of (±)-trans-N1-(tert-butoxycarbonyl)-N2-[(5-chloroindol-2-yl)-carbonyl]-1,2-cyclohexanediamine (5.18 g) in dichloromethane (100 ml) at room temperature. After stirring for 2 days, the reaction mixture was concentrated under reduced pressure, diethyl ether (300 ml) was added to the resultant residue, and colorless precipitate formed was collected by filtration and dried to obtain the title compound (4.30 g) as a colorless solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure, diethyl ether (300 ml)
  2. additionwas added to the resultant residue, and colorless precipitate
  3. customformed
  4. filtrationwas collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-cbf29c6d023345f1ac021a1cdbfe2508
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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