Triethylamine → 3-(Quinolin-4-yloxy)propyl mesylate

HRID 40798Notes

Reaction equation

HRID 40798 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([O:11][CH2:12][CH2:13][CH2:14][OH:15])=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[S:24]([O:15][CH2:14][CH2:13][CH2:12][O:11][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1)(=[O:26])(=[O:25])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 685762503-(Quinolin-4-yloxy)propan-1-ol

Product 1

HCID 866295403-(Quinolin-4-yloxy)propyl mesylateYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the 3-(quinolin-4-yloxy)propan-1-ol obtained in step a) (0.5298 g, 2.6 mmol) was treated with triethylamine (0.60 mL) and methanesulfonyl chloride (0.55 g, 4.8 mmol) in dichloromethane (5 mL). After the starting material was consumed, the reaction was diluted with dichloromethane, washed with water, aq NaHCO3 and evaporated. The residue was purified by column chromatography on SiO2 and eluted with ethyl acetate. The product was obtained as a light yellow solid (0.3868 g, 53%). 1H NMR (400 MHz, CDCl3): 2.43 (2H, m), 3.00 (3H, s), 4.38 (2H, t, J=5.8 Hz), 4.55 (2H, t, J=5.8 Hz), 6.80 (1H, d, J=5.5 Hz), 7.55 (1H, t, J=8.0 Hz), 7.75 (1H, ddd, J=1.2, 7.0, 8.2 Hz), 8.20 (1H, d, J=8.4 Hz), 8.13 (1H, d, J=8.4 Hz), 8.77 (1H, d, J=5.3 Hz).

Workup

  1. customAfter the starting material was consumed
  2. additionthe reaction was diluted with dichloromethane
  3. washwashed with water, aq NaHCO3
  4. customevaporated
  5. customThe residue was purified by column chromatography on SiO2
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-ae7e113c14d440ad9ae8dca4b19af461
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

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