Ammonium Acetate → 1-[7-(1-Aminoethyl)-5-chloroquinolin-8-yl]-4-phenylpiperidin-4-ol

HRID 1192558Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][C:18]([OH:27])([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:34].[Na+]>CO.C(#N)C>[NH2:34][CH:12]([C:10]1[C:9]([N:15]2[CH2:20][CH2:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([OH:27])[CH2:17][CH2:16]2)=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([Cl:1])[CH:11]=1)[CH3:13]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1-[5-chloro-8-(4-hydroxy-4-phenylpiperidin-1-yl) quinolin-7-yl]ethanone (37 mg, 0.097 mmol) and ammonium acetate (74.9 mg, 0.971 mmol) in methanol (0.55 mL) and acetonitrile (0.55 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, sodium cyanoborohydride (12.2 mg, 0.194 mmol). The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature and quenched with sat. sodium bicarbonate, extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness (35 mg, 94%). LCMS calculated for C22H25ClN3O (M+H)+: m/z=382.2; Found: 382.1.

Workup

temperatureAfter cooling to room temperature
temperatureThe reaction was heated at 65° C. for another 4 hours
temperaturecooled to room temperature
customquenched with sat. sodium bicarbonate
extractionextracted with dichloromethane
dry with materialThe combined extracts were dried over magnesium sulfate
customevaporated to dryness (35 mg, 94%)

Sources & evidence

ORD record: ord-1c2cc74f5b8849cbbd9debfe38efce87
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

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