Diethyl Ether → 5-(2-Aminopropyl)thiophene-2-carboxamide

HRID 373972Notes

Reaction equation

HRID 373972 reaction equation
[N:1]([CH:4]([CH3:14])[CH2:5][C:6]1[S:10][C:9]([C:11]([NH2:13])=[O:12])=[CH:8][CH:7]=1)=[N+]=[N-].N.C(OCC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[NH2:1][CH:4]([CH3:14])[CH2:5][C:6]1[S:10][C:9]([C:11]([NH2:13])=[O:12])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 19809153HCID 19809153, compound

Product 1

HCID 198091105-(2-Aminopropyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

For the preparation of the amine starting material of Example 10f, α-methyl-2-thiophenethanol, acetyl chloride and aluminum chloride were reacted in methylene chloride to give (RS)-2-(5-acetyl-2-thienyl)-1-methylethyl acetate. The resulting acetate was saponified with sodium hydroxide in methanol to give 5-[(RS)-2-hydroxypropyl]-2-thienyl methyl ketone which was subsequently reacted with p-toluenesulfonyl chloride to give (RS)-2-(5-acetyl-2-thienyl)-1-methylethyl-p-toluenesulfonate, m.p. 101°-103°. With sodium azide in dimethylsulfoxide there was obtained therefrom 5-[(RS)-2-azidopropyl]-2-thienyl methyl ketone which was oxidized with bromine in sodium hydroxide solution to give 5-[(RS)-2-azidopropyl]-2-thiophenecarboxylic acid. With thionyl chloride, there was obtained therefrom the corresponding acid chloride and from this there was prepared with ammonia 5-[(RS)-2-azidopropyl]-2-thiophenecarboxamide, m.p. 79°-80° C., from diethyl ether. Treatment with triphenylphosphine and hydrolysis gave 5-[(RS)-2-aminopropyl]-2-thiophenecarboxamide, m.p. 91°-92° from acetonitrile.

Sources & evidence

ORD record
ord-3784a6ffd89d4c008d669871e3209bfd
Source dataset
uspto-grants-1992_11
Patent number
US05166218

Reaction notes

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