Hydrochloric Acid → HCID 68161466, compound

HRID 2041703Notes

Reaction equation

HRID 2041703 reaction equation
CC([N:5]([CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N:19]3[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]3)[CH:17]=2)[N:12]([C:25](=[O:27])[CH3:26])[CH:11]([CH3:28])[CH2:10]1)C(=O)[O-])(C)C.[ClH:29]>ClCCl>[ClH:29].[ClH:29].[C:25]([N:12]1[C:13]2[C:18](=[CH:17][C:16]([N:19]3[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]3)=[CH:15][CH:14]=2)[C@H:9]([NH2:5])[CH2:10][C@@H:11]1[CH3:28])(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86669441HCID 86669441, compound

Product 1

HCID 68161466HCID 68161466, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1,1-dimethylethyl[1-acetyl-2-methyl-6-(4-methyl-1H-imidazol-1-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 62) (5.7 g, 14.83 mmol) in dichloromethane (DCM) (40 mL) was treated at room temperature with HCl (4N in 1,4-dioxane, 20 ml, 80 mmol). An ice bath was used during the addition to keep the temperature below 30° C. Once the addition was completed, DCM (20 mL) was added and the resulting mixture was stirred at room temperature for 2 h then concentrated in vacuo to give (cis)-1-acetyl-2-methyl-6-(4-methyl-1H-imidazol-1-yl)-1,2,3,4-tetrahydro-4-quinolinamine di-hydrochloride as (5.12 g, 14.33 mmol, 97%) as a white solid.

Workup

  1. additionAn ice bath was used during the addition
  2. customthe temperature below 30° C
  3. additionOnce the addition
  4. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-653019b739fc4358a03ecbafb0c27a8a
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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