Dimethylamine → HCID 23505612, compound

HRID 1993333Notes

Reaction equation

HRID 1993333 reaction equation
Cl[CH2:2][C:3]1[N+:12]([O-:13])=[C:11]([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:10]2[C:5](=[CH:6][C:7]3[O:25][CH2:24][O:23][C:8]=3[CH:9]=2)[N:4]=1.[CH3:26][NH:27][CH3:28]>C1COCC1>[CH3:26][N:27]([CH2:2][C:3]1[N+:12]([O-:13])=[C:11]([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:10]2[C:5](=[CH:6][C:7]3[O:25][CH2:24][O:23][C:8]=3[CH:9]=2)[N:4]=1)[CH3:28]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 23505617HCID 23505617, compound

Product 1

HCID 23505612HCID 23505612, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 2-chloromethyl-6,7-methylenedioxy-4-(3,4-methylenedioxyphenyl)quinazoline-3-oxide (200 mg, 0.55 mmol), in THF (6 mL), was added dimethylamine (2M in THF, 2 mL, 4 mmol). The mixture was stirred at 65° C. for 2 h. After cooling, the solvent was evaporated and the residue was purified by column chromatography on silica gel (hexane:acetone 4:1); mp 205-210° C. 1H NMR (CDCl3) 7.41 (s, 1H), 6.90-7.06 (m, 4H), 6.78 (s 1H), 6.11 (s, 2H), 6.08 (s, 2H), 4.05 (s, 2H), 2.52 (s, 6H).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated
  3. customthe residue was purified by column chromatography on silica gel (hexane:acetone 4:1)

Sources & evidence

ORD record
ord-d84a1c437870473cbef8f023194e04e4
Source dataset
uspto-grants-2010_01
Patent number
US07652006B2

Reaction notes

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