Ethyl formate → 2-amino-N-formyl-N-methyl-alpha-(3-methyl-2-thienyl)benzeneethanamine
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:12]1[S:13][CH:14]=[CH:15][C:16]=1[CH3:17])[NH:10][CH3:11].[CH:18](OCC)=[O:19]>>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:12]1[S:13][CH:14]=[CH:15][C:16]=1[CH3:17])[N:10]([CH:18]=[O:19])[CH3:11]Participants
3
Procedure
A stirred solution of 5.00 g of 2-amino-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine and 235 ml of ethyl formate was refluxed for 8 hours. Volatile components were removed at 60° C. on a rotary evaporator. Thin layer chromatography (silica gel, ethyl acetate as the eluent) of the resultant oil indicated a multi-component mixture. HPLC of the mixture (Water's Associates Prep LC/System 500, silica gel, elution with ethyl acetate) permitted component separation. The faster eluting fractions were concentrated to an oil which crystallized upon standing. Recrystallization from methanol-water afforded 1.2 g of 2-amino-N-formyl-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine, mp 111°-112° C.
Workup
- customVolatile components were removed at 60° C. on a rotary evaporator
- washHPLC of the mixture (Water's Associates Prep LC/System 500, silica gel, elution with ethyl acetate)
- customcomponent separation
- washThe faster eluting fractions
- concentrationwere concentrated to an oil which
- customcrystallized
- customRecrystallization from methanol-water
Sources & evidence
- ORD record
- ord-128213b5269548b0aa83db64d803b120
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05292760
Reaction notes
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