Potassium Carbonate → HCID 18932897, compound

HRID 1597991Notes

Reaction equation

HRID 1597991 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][N:9]2[C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH2:22])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1.[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27]Cl.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][N:9]2[C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:22][CH2:27][CH2:26][CH2:25][N:24]([CH3:29])[CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 18932794HCID 18932794, compound

Product 1

HCID 18932897HCID 18932897, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

4-(6-Chloro-2,3-dihydro-indol-1-yl)-quinazolin-6-ylamine hydrochloride (0.525 g, 1.58 mmol) was combined with 2 mL of freshly distilled 3-dimethylaminopropyl chloride and heated to 120° C. for 1 hour. Yellow liquid was poured off and the remaining red glass was dissolved in water, basified to pH 11 with potassium carbonate, extracted with chloroform (2×50 mL), washed with brine, dried over magnesium sulfate, filtered and stripped to give 0.272 g yellow foam containing starting material and mono- and di-alkylated products. This foam was filtered through silica gel using chloroform, then the product was washed through the silica gel with 40% v/v methanol in chloroform and concentrated in vacuo. The residue was dissolved in methanol, treated with 1N HCl in methanol diluted with diethyl ether, filtered and dried under vacuum to afford a bright yellow solid, 0.0995 g (15%): M.P. 230° C. (dec):LC-MS: 382 (MH+), 384 ((M+2)H+).

Workup

  1. additionYellow liquid was poured off
  2. extractionextracted with chloroform (2×50 mL)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-38bb5c1f971b4bd68252219167d9fa93
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

Loading…