HCID 20483366, compound → HCID 4156105, compound

HRID 647821Notes

Reaction equation

Cl.Cl.Cl.[CH2:4]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH2:24])[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:25]([O-])=O.[Na+]>O>[CH2:4]([N:11]1[CH2:12][CH2:13][CH:14]([N:17]2[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]=[N:25]2)[CH2:15][CH2:16]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In this reference example, 2.0 g of 1-benzyl-4-(2-aminoanilino)-piperidine trihydrochloride obtained in the same manner as that of Reference Example 1 is dissolved in 30 ml of water and the solution is cooled to 0° C. To the cooled solution, 5 ml of a solution of 360 mg of sodium nitrite in 5 ml of water is added dropwise under the current of nitrogen gas over a period of 30 minutes. After completion of the dropwise addition, the reaction mixture is stirred at 0°-5° C. for one hour and then adjusted to pH 10.7. The reaction mixture is extracted with 30 ml of chloroform three times. The chloroform layer is washed with water and dried. The chloroform layer is concentrated to dryness under reduced pressure. The residue is subjected to silica gel chromatography [Wako Gel C-200, 150 ml, with a chloroform-methanol (10:1) as the eluent]. The eluate is concentrated to obtain 0.71 g of the desired product.

Workup

additionAfter completion of the dropwise addition
extractionThe reaction mixture is extracted with 30 ml of chloroform three times
washThe chloroform layer is washed with water
customdried
concentrationThe chloroform layer is concentrated to dryness under reduced pressure
concentrationThe eluate is concentrated

Sources & evidence

ORD record: ord-ec40f8f6cf5d4a15a1704bc4353c757e
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04410528

Reaction notes

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