Water → HCID 67439261, compound

HRID 1664795Notes

Reaction equation

[O-:1][C:2]#N.[K+].[C:5]([C:7]1([NH:23][CH3:24])[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH2:8]1)#[N:6].[OH2:25]>C(O)(=O)C>[CH3:24][N:23]1[C:7]2([CH2:8][CH2:9][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:14])[CH2:11][CH2:12]2)[C:5](=[O:25])[NH:6][C:2]1=[O:1]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of potassium cyanate (5.74 g, 70.8 mmol) in water (9 mL) was added dropwise to a solution of the hydrochloride salt of benzyl 4-cyano-4-(methylamino)piperidine-1-carboxylate (9.68 g, 35.4 mmol) in acetic acid (27 mL). The reaction mixture was heated at 50° C. After 1 h, the mixture was poured into cold water (200 mL). The mixture was extracted with ethyl acetate (4×), and the combined organic extracts were dried over magnesium sulfate and concentrated. A solution of HCl (10% in water; 40 mL) was added and the mixture was heated at 50° C. After 15 min, the reaction mixture was cooled to ambient temperature. The precipitated solid was filtered, washed with water, and dried under reduced pressure to give the title compound. MS 318.1 (M+1).

Workup

extractionThe mixture was extracted with ethyl acetate (4×)
dry with materialthe combined organic extracts were dried over magnesium sulfate
concentrationconcentrated
additionA solution of HCl (10% in water; 40 mL) was added
temperaturethe mixture was heated at 50° C
waitAfter 15 min
temperaturethe reaction mixture was cooled to ambient temperature
filtrationThe precipitated solid was filtered
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-124da3f607b64eac81797caf4cf4c3ff
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039460B2

Reaction notes

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