Dimethylformamide → 4-(1-Acetyl-piperidine-4-carbonyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine-2-carbaldehyde

HRID 983063Notes

Reaction equation

HRID 983063 reaction equation
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([C:11]([CH:13]3[CH2:18][CH2:17][N:16]([C:19](=[O:21])[CH3:20])[CH2:15][CH2:14]3)=[O:12])[C:4]=2[CH:3]=[CH:2]1.O=P(Cl)(Cl)Cl.CN([CH:30]=[O:31])C>[Au]>[C:19]([N:16]1[CH2:15][CH2:14][CH:13]([C:11]([N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]3[NH:1][C:2]([CH:30]=[O:31])=[CH:3][C:4]2=3)=[O:12])[CH2:18][CH2:17]1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 225618581-[4-(5,6,7,8-Tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)piperidin-1-yl]-ethanone

Product 1

HCID 225617494-(1-Acetyl-piperidine-4-carbonyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 23985GoldCatalyst

Procedure

1-[4-(5,6,7,8-Tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)piperidin-1-yl]-ethanone (1.1 g) was formylated with POCl3 (186 μL, 1.2 eq.) and DMF using standard Vismierer condition to give 240 mg of 4-(1-acetyl-piperidine-4-carbonyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine-2-carbaldehyde as a gold colored solid.

Sources & evidence

ORD record
ord-768641e59b3e4f7db946970b4347fe2e
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

Loading…