Methylamine → HCID 13225517, compound

HRID 464179Notes

Reaction equation

HRID 464179 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[CH2:6][N:7]=[C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:9]3[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:10]=3[C:11]=2[N:12]=1.[CH3:25][NH2:26]>CN(C)C=O>[Cl:17][C:15]1[CH:14]=[CH:13][C:10]2[C:11]3[N:12]=[C:2]([NH:26][CH3:25])[N:3]=[CH:4][C:5]=3[CH2:6][N:7]=[C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:9]=2[CH:16]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13225515HCID 13225515, compound

Product 1

HCID 13225517HCID 13225517, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1 g (0.00279 mol) of 2,9-dichloro-7-(2-fluorophenyl)-5H-pyrimido[5,4-d][2]benzazepine in 4 ml of N,N-dimethylformamide was cooled in an ice bath and saturated with methylamine. After 64 hr at room temperature, 50 ml of ice water was added and the reaction was filtered. The precipitate was partitioned between 50 ml of dichloromethane and 50 ml of water, and the organic layer was washed with 25 ml of brine solution, dried and evaporated to dryness. The oil was crystallized from ether and then recrystallized from dichloromethane/ether and then from methanol to give the end product as white prisms, mp 172°-179°.

Workup

  1. filtrationthe reaction was filtered
  2. customThe precipitate was partitioned between 50 ml of dichloromethane and 50 ml of water
  3. washthe organic layer was washed with 25 ml of brine solution
  4. customdried
  5. customevaporated to dryness
  6. customThe oil was crystallized from ether
  7. customrecrystallized from dichloromethane/ether

Sources & evidence

ORD record
ord-5f3819c5f6f546fa86d0b04e53ff5d4f
Source dataset
uspto-grants-1985_10
Patent number
US04546183

Reaction notes

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