Acetyl chloride → HCID 23091680, compound

HRID 272939Notes

Reaction equation

HRID 272939 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[N:5]1([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3([CH2:26][NH:27][CH2:28][CH3:29])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C>C1COCC1>[CH2:28]([N:27]([CH2:26][C:20]1([C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][CH2:11][CH2:10][N:5]3[CH2:9][CH2:8][CH2:7][CH2:6]3)=[CH:19][CH:18]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:1](=[O:3])[CH3:2])[CH3:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11523085HCID 11523085, compound

Product 1

HCID 23091680HCID 23091680, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (14 μL, 0.20 mmol) was added dropwise to a solution of N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)ethanamine (70 mg, 0.20 mmol) and triethylamine (28 μL, 0.20 mmol) in THF (0.50 mL) at 0° C. and the reaction stirred for 2 hours. The reaction was quenched using NaHCO3 (10 mL), extracted with dichloromethane (3×10 mL) and the organic extracts dried over Na2SO4, filtered and concentrated in vacuo. The compound was purified by column chromatography on silica, eluting with DCM/MeOH/NH3 (95:5:0.5) to provide the title compound as a clear oil (33 mg, 42%). 1H NMR complicated by the presence of rotamers. 1H NMR (400 MHz, CDCl3) δ 7.20-7.12 (m, 2H), 6.92-6.86 (m, 2H), 4.06-4.00 (m, 2H), 3.88-3.76 (m, 2H), 2.56-2.48 (m, 2H), 3.42 (s, 2H), 2.66 (t, 2H), 2.58-2.52 (m, 4H), 2.48 (quartet, 2H), 2.08 (s, 3H), 2.06-1.92 (m, 6H), 1.84-1.76 (m, 4H), 0.98 (t, 0.6H) 0.86 (t, 2.4H). HRMS (ESI+) 389.2799 (M+H)+.

Workup

  1. customThe reaction was quenched
  2. extractionextracted with dichloromethane (3×10 mL)
  3. dry with materialthe organic extracts dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe compound was purified by column chromatography on silica
  7. washeluting with DCM/MeOH/NH3 (95:5:0.5)

Sources & evidence

ORD record
ord-1955ab5103dc4c4ba0bc5236032daa4e
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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