Formamide → HCID 13787477, compound

HRID 1905918Notes

Reaction equation

HRID 1905918 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1.[CH:14](N)=[O:15]>C(O)=O>[CH2:7]([N:4]1[CH2:5][CH2:6][CH:2]([NH:1][CH:14]=[O:15])[CH2:3]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 713FormamideHCID 27566131-Benzyl-3-aminopyrrolidine

Product 1

HCID 13787477HCID 13787477, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

3-Amino-1-benzylpyrrolidine [J. Med. Chem., 11, 1034 (1968)] was allowed to react with formic acid and formamide to give 1-benzyl-3-formylaminopyrrolidine. This compound was reduced with sodium bis(2-methoxyethoxy)-aluminium hydride to give 1-benzyl-3-methylaminopyrrolidine, b.p. 134°-136° C./5-6 mmHg. This compound was treated with acetic anhydride to give 3-(N-acetyl-N-methylamino)-1-benzylpyrrolidine, b.p. 144°-147° C./0.5 mmHg. This compound was hydrogenated catalytically in the presence of 5% palladium-carbon to give 3-(N-acetyl-N-methylamino)-pyrrolidine as an oil.

Sources & evidence

ORD record
ord-91504aca88f34f30ba8a1de3a7048b4f
Source dataset
uspto-grants-1987_03
Patent number
US04649144

Reaction notes

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