Water → HCID 59837470, compound

HRID 272954Notes

Reaction equation

HRID 272954 reaction equation
C(N1CC[CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3([CH2:23][NH:24][CH3:25])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)CC1)(C)C.[CH2:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH3:27].[C:33](OC(=O)C)(=[O:35])[CH3:34].O.Cl[CH2:42]Cl>>[CH:26]([N:28]1[CH2:31][CH2:32][CH:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3([CH2:23][N:24]([CH3:25])[C:33](=[O:35])[CH3:34])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[CH:15][CH:16]=2)[CH2:30][CH2:29]1)([CH3:42])[CH3:27]

Participants

6

Reactant 5

HCID 962WaterHCID 6344Dichloromethane2×HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11688814HCID 11688814, compound

Product 1

HCID 59837470HCID 59837470, compoundYield 83%

Procedure

To a stirred solution of N-[(4-{4-[(1-isopropylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-yl)methyl]-N-methylamine (120 mg, 0.347 mmol) and triethylamine (121 μl, 0.867 mmol) in dichloromethane (1 ml) at 0° C. was added dropwise acetic anhydride (36 μl, 0.382 mmol). The reaction mixture was warmed to ambient temperature until reaction complete. Water (1 ml) and dichloromethane (15 ml) added to the reaction, the extracted with saturated NaHCO3 (2×10 ml). Organic washings were dried over Na2SO4 and concentrated in vacuo to give the title compound as an oil (113 mg, 83%). 1H NMR (400 MHz, CDCl3) δ 7.10-7.22 (2 doublets due to rotamers, 2H), 6.80 (d, 2H), 4.24-4.38 (m, 1H), 3.79-3.80 (m, 2H), 3.42-3.60 (m, 2H), 2.70-2.90 (m, 3H), 2.39-2.48 (m, 2H), 3.20-3.35 (singlet and doublet due to rotamers, 3H), 1.75-2.10 (m, 11H), 1.10 (d, 6H).

Workup

  1. extractionthe extracted with saturated NaHCO3 (2×10 ml)
  2. dry with materialOrganic washings were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae8cb82264ed442d8e3c85555a2e94fd
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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