Benzyl Alcohol → HCID 59178855, compound

HRID 1947660Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:3]=1.[C:27]1([CH2:33][OH:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[H-].[Na+]>CN(C=O)C>[CH2:33]([O:34][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:3]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 30 °C

Procedure

The tert-butyl 1′-(6-chloropyrimidin-4-yl)-4,4′-bipiperidine-1-carboxylate (100 mg, 0.26 mmol), phenylmethanol (0.031 mL, 0.29 mmol) were added to DMF (2.6 mL), and then sodium hydride (7 mg, 0.29 mmol) was added to the mixture. The reaction was heated to 30° C. for 30 min The reaction crude was cooled down to r.t. and quenched with ice ammonia chloride solution (10 mL) and extracted with ethyl acetate (10 mL). The organic phase was washed with brine (10 mL, ×1), dried over magnesium sulfate, filtered and concentrated by rotavapor. The crude mixture was purified by preparative TLC with 30% ethylacetate:hexane to yield the title compound.

Workup

customThe reaction crude
temperaturewas cooled down to r.t.
customquenched with ice ammonia chloride solution (10 mL)
extractionextracted with ethyl acetate (10 mL)
washThe organic phase was washed with brine (10 mL, ×1)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated by rotavapor
customThe crude mixture was purified by preparative TLC with 30% ethylacetate

Sources & evidence

ORD record: ord-720633936e2d4bdf90e70202ce4a9b2b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399485B2

Reaction notes

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