Hydrochloric Acid → Valeryl chloride

HRID 1940189Notes

Reaction equation

HRID 1940189 reaction equation
[ClH:1].[C:2]([C:4]1([NH:9][C:10](=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:8][CH2:7][CH2:6][CH2:5]1)#[N:3].C1(=O)CCCC1>C(O)C>[NH2:9][C:4]1([C:2]#[N:3])[CH2:8][CH2:7][CH2:6][CH2:5]1.[C:10]([Cl:1])(=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8452CyclopentanoneHCID 11790092N-(1-Cyanocyclopentyl)pentanamide

Product 2

HCID 61186Valeryl chlorideHCID 21068971-Aminocyclopentanecarbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

9.39 g (39 mmol) of a freshly prepared solution of hydrogen chloride in ethanol (15.15 percent by weight) was added to 6.80 g (30 mmol) of N-(1-cyanocyclopentyl)-pentanamide (prepared from cyclopentanone by means of a Strecker synthesis to give 1-aminocyclopentanecarbonitrile and acylation with pentanoyl chloride, content 85.7 percent) in 28 g of anhydrous ethanol. The mixture was heated to 50° C. under nitrogen and stirred at this temperature for 3.1 hours. It was then cooled to 1° C. and left to stand at this temperature for 1 hour. The product which had precipitated out was filtered off, washed with 10 ml of ice-cold ethanol and dried at 40° C./24 mbar. The yield of the product was 4.05 g (58 percent) of colorless crystals, content 98.3 percent (HPLC).

Sources & evidence

ORD record
ord-e041fecba6224daba9f75e52b50d01a6
Source dataset
uspto-grants-1997_12
Patent number
US05698704

Reaction notes

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