Hydrochloric Acid → 6-(2-(Chloro(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine hydrochloride

HRID 1028950Notes

Reaction equation

HRID 1028950 reaction equation
[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=3[CH:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)O)[CH:8]=2)[N:3]=1.[ClH:33].S(Cl)([Cl:36])=O>C(Cl)Cl.CC(O)C>[ClH:36].[Cl:33][CH:25]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([CH3:24])[C:18]=1[C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH2:1])[C:11]([N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)=[CH:10]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 67350995(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanol

Product 1

HCID 673478476-(2-(Chloro(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine hydrochloride

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanol (0.155 g, 0.364 mmol) in DCM was treated with 0.4 mL of 5N HCl in iPrOH. The mixture was concentrated in vacuo and azeotroped 3× with DCM. The resulting yellow solid was treated again with DCM (1.21 mL) and thionyl chloride (0.80 mL, 10.93 mmol) was added dropwise, and the reaction mixture was stirred for 30 min at ambient temperature for 1 h and concentrated in vacuo. The residue was azeotroped 2× with DCM and dried under vacuum to afford crude 6-(2-(chloro(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine hydrochloride which was used without further purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customazeotroped 3× with DCM
  3. additionwas added dropwise
  4. concentrationconcentrated in vacuo
  5. customThe residue was azeotroped 2× with DCM
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b94c6fa09af54b6c9a80a03c71747bd4
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

Loading…