Acetyl chloride → HCID 59713388, compound

HRID 2223050Notes

Reaction equation

CN1CC[O:5][CH2:4][CH2:3]1.[CH3:8][C:9]1[CH:10]=[C:11]([CH:32]=[C:33]([CH3:35])[CH:34]=1)[C:12]([C:14]1([NH:20][C:21](=[O:31])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:23]=2[CH3:30])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)=[O:13].C(Cl)(=O)C>>[C:4]([N:17]1[CH2:16][CH2:15][C:14]([NH:20][C:21](=[O:31])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:23]=2[CH3:30])([C:12](=[O:13])[C:11]2[CH:10]=[C:9]([CH3:8])[CH:34]=[C:33]([CH3:35])[CH:32]=2)[CH2:19][CH2:18]1)(=[O:5])[CH3:3]

Participants

Reactant 3

HCID 6367Acetyl chloride

HCID 79724-Methylmorpholine

HCID 10429879HCID 10429879, compound

Product 1

HCID 59713388HCID 59713388, compound

Procedure

A 25 mL vial was charged with a magnetic stir bar and morpholinomethylpolystyrene (PS-NMM, ˜300 mg, 1.92 mmol/g, 0.6 mmol). A solution of N-[4-(3,5-dimethyl-benzoyl)-piperidin-4-yl]-3-methoxy-2-methyl-benzamide (76 mg, 0.2 mmol in 2 mL CH2Cl2) was added, followed by acetyl chloride (16 μL, 0.22 mmol). The mixture was stirred for 2 days, filtered, and fractionated on a 2 g silica gel cartridge, eluting with a 0-100% ethyl acetate in hexanes gradient to provide N-[1-acetyl-4-(3,5-dimethyl-benzoyl)-piperidin-4-yl]-3-methoxy-2-methyl-benzamide. 1H NMR (500 MHz, CDCl3) δ(ppm): 7.6 (s, 2H), 7.15 (m, 2H), 6.87 (d, 2H), 6.7 (d, 1H), 4.17 (dt, 1H), 3.8 (s, 3H), 3.78 (m, 1H), 3.45 (t, 1H), 3.25 (t, 1H), 2.5 (m, 1H), 2.35 (m, 1H), 2.32 (s, 6H), 2.2 (m, 1H), 2.17 (m, 1H), 2.05 (s, 3H), 1.92 (s, 3H).

Workup

additionA 25 mL vial was charged with a magnetic stir bar
filtrationfiltered
washeluting with a 0-100% ethyl acetate in hexanes gradient

Sources & evidence

ORD record: ord-ea717c3abf024620ad49e67971fb6a96
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375093B2

Reaction notes

Loading…