Acetyl chloride → N-{bicyclo[1.1.1]pentan-1-yl}acetamide

HRID 62612Notes

Reaction equation

HRID 62612 reaction equation
[C:1]12([NH2:6])[CH2:5][CH:3]([CH2:4]1)[CH2:2]2.[C:7](Cl)(=[O:9])[CH3:8].C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[C:1]12([NH:6][C:7](=[O:9])[CH3:8])[CH2:5][CH:3]([CH2:4]1)[CH2:2]2

Participants

7

Reactant 5

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 11469065Bicyclo(1.1.1)pentan-1-amine

Product 1

HCID 86287956N-{bicyclo[1.1.1]pentan-1-yl}acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The commercially available bicyclo[1.1.1]pentan-1-amine can be coupled with an appropriate carboxylic acid or acid chloride, such as acetyl chloride in the presence of base (for example, K2CO3, Na2CO3, NaHCO3, TEA, pyridine, and the like) to give N-(bicyclo[1.1.1]pentan-1-yl)acetamide (4) (Scheme 3).

Sources & evidence

ORD record
ord-ecc5f7200a6f4f7faa97130c2864c5dd
Source dataset
uspto-grants-2016_09
Patent number
US09447026B2

Reaction notes

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