4-Chlorobenzoyl chloride → HCID 67773171, compound

HRID 1808857Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][NH:12][C@@H:13]([CH2:22][CH2:23][CH3:24])[CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:12]([C@@H:13]([CH2:22][CH2:23][CH3:24])[CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([OH:21])[CH2:19][CH2:20]2)[CH3:11])=[O:7])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Chlorobenzoyl chloride (1.683 mL, 13.12 mmol) was added to a solution of (S)-1-(2-(methylamino)pentyl)piperidin-4-ol (Compound J6) (2.629 g, 13.12 mmol) and TEA (3.66 mL, 26.25 mmol) in DCM (25 mL) at 0° C. A white slurry was formed. The reaction was stirred for 45 min at 0° C. and was then allowed to attain rt. The reaction was stirred overnight and was then quenched by addition of NaHCO3 (8% aq., 25 mL). The aqueous phase was extracted with DCM. The organic phases were pooled, dried (MgSO4), filtered and evaporated under reduced pressure. The crude product was chromatographed to give the title product (3.13 g, 70.3%) as a colourless glue. 1H NMR (400 MHz, CD3OD) 0.87, 0.99, 1.17-1.33, 1.35-1.63, 1.71-1.90, 1.95-2.15, 2.15-2.36, 2.43-2.51, 2.52-2.68, 2.71-2.80, 2.89, 2.99-3.08, 3.51-3.64, 3.68-3.77, 4.87-4.97, 7.08-7.24, 7.37-7.51. HRMS (M+H)+: calculated 339.1839. found 339.1827.

Workup

customA white slurry was formed
customto attain rt
stirringThe reaction was stirred overnight
customwas then quenched by addition of NaHCO3 (8% aq., 25 mL)
extractionThe aqueous phase was extracted with DCM
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated under reduced pressure
customThe crude product was chromatographed

Sources & evidence

ORD record: ord-f392527fd5b444a186d1be1552f77684
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08361998B2

Reaction notes

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