Water → HCID 59837512, compound

HRID 272956Notes

Reaction equation

HRID 272956 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3([CH2:23][NH:24][CH2:25][CH3:26])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C(N([CH2:32][CH3:33])CC)C.C(OC(=O)C)(=[O:36])C.O>ClCCl>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3([CH2:23][N:24]([CH2:32][CH3:33])[C:25](=[O:36])[CH3:26])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11574068HCID 11574068, compound

Product 1

HCID 59837512HCID 59837512, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-[(4-{4-[(1-isopropylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-yl)methyl]-N-ethylamine (102 mg, 0.283 mmol) and triethylamine (99 μl. 0.708 mmol) in dichloromethane (1 ml) was added dropwise acetic anhydride (29 μl, 0.312 mmol). Reaction left at ambient temperature for 4 hours until reaction complete. Water (1 ml) and dichloromethane (10 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 (107 mg, 94%). 1H NMR (400 MHz, CD3OD) δ 7.20-7.31 (multiplet due to rotamers, 2H), 6.92-7.00 (multiplet due to rotamers, 2H), 4.36-4.46 (m, 1H), 3.70-3.88 (m, 2H), 3.20-3.55 (several peaks due to rotamers, 4H), 2.78-2.90 (m, 3H), 2.60, (q, 2H), 2.25-2.52 (multiple peaks due to rotamers, 2H), 1.70-2.10 (multiple peaks, 11H), 1.10 (d, 6H), 0.80-1.00 (two triplets due to rotamers, 3H).

Workup

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

Sources & evidence

ORD record
ord-d4cfe6f2c55c424eb2505738eea14aa4
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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