Water → HCID 21476266, compound

HRID 2293110Notes

Reaction equation

HRID 2293110 reaction equation
[CH3:1]I.C(=O)([O-])[O-].[K+].[K+].O.[C:10]12([N:20](C)[C:21]3[C:22]([NH2:27])=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2>CN(C=O)C>[C:10]12([NH:20][C:21]3[C:22]([NH:27][CH3:1])=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:17][CH:16]3[CH2:18][CH:12]([CH2:13][CH:14]([CH2:15]3)[CH2:19]1)[CH2:11]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21476257HCID 21476257, compound

Product 1

HCID 21476266HCID 21476266, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (0.564 ml) was added to a mixture of intermediate 11 (2 g) and potassium carbonate (1.75 g) in dry DMF (8 ml) at 23° under nitrogen. After 4.5 h, the mixture was poured into water (100 ml) and extracted with EA (2×100 ml). The combined extracts were washed with water and saturated brine then dried and evaporated. The residue was chromatographed with hexane- EA (8:1 to 6:1 to 4:1) as eluent to give a 70:30 mixture of the title compound with N-adamantan-1-yl-N-methylbenzene-1,2-diamine (904 mg) as a yellow solid, m.p. 68°-76° dec.

Workup

  1. extractionextracted with EA (2×100 ml)
  2. washThe combined extracts were washed with water and saturated brine
  3. customthen dried
  4. customevaporated
  5. customThe residue was chromatographed with hexane- EA (8:1 to 6:1 to 4:1) as eluent
  6. customto give

Sources & evidence

ORD record
ord-2c94db15832e443aa33d405625748d8f
Source dataset
uspto-grants-1997_11
Patent number
US05686449

Reaction notes

Loading…