Diisopropylamine → HCID 58266325, compound

HRID 1888420Notes

Reaction equation

HRID 1888420 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:16])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(NC(C)C)(C)C.C1C=CC(N[S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:16][S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 582667373-Methoxy-4-piperidin-1-ylmethylphenol

Product 1

HCID 58266325HCID 58266325, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-methoxy-4-piperidin-1-ylmethylphenol (456 mg, 2.06 mmol) and diisopropylamine (0.77 mL, 4.54 mmol) in DCM (10 mL) at 0° C. was added N-phenyltriflamide (958 mg, 2.68 mmol). After the addition was complete the reaction mixture was allowed to warm to ambient temperature and then stirred overnight. The reaction mixture was concentrated under reduced pressure and then purified by flash chromatography (silica, 40 g column, ISCO, 0-10% methanol in DCM) to afford the title compound as a colourless oil (408 mg, 56%). 1H NMR (CDCl3, 300 MHz): 7.60 (d, J=8.4 Hz, 1H), 6.93 (dd, J=8.4, 2.4 Hz, 1H), 6.80 (d, J=2.4 Hz, 1H), 3.93 (s, 2H), 3.89 (s, 3H), 2.87-2.74 (m, 4H), 1.82-1.75 (m, 4H), 1.57-1.50 (m, 2H).

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by flash chromatography (silica, 40 g column, ISCO, 0-10% methanol in DCM)

Sources & evidence

ORD record
ord-cd996b43b8c64138afb0c21afff5034b
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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