Diisopropylamine → HCID 58266325, compound

HRID 1505883Notes

Reaction equation

HRID 1505883 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%). 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-097367794d5b4a8cb939e01cd4c57095
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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