Dimethylamine → HCID 59593473, compound

HRID 2261244Notes

Reaction equation

HRID 2261244 reaction equation
Br[CH2:2][C:3]1[O:7][C:6]([C:8]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])=[N:5][CH:4]=1.[CH3:22][NH:23][CH3:24]>C1COCC1>[CH:16]1([C:8]([C:6]2[O:7][C:3]([CH2:2][N:23]([CH3:24])[CH3:22])=[CH:4][N:5]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 59593469HCID 59593469, compound2×

Product 1

HCID 59593473HCID 59593473, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (5-bromomethyl-oxazol-2-yl)-cyclohexyl-phenyl-methanol (Intermediate 4) (3.2 g, 9.2 mmol) in THF (40 mL) was treated with a 2 M solution of dimethylamine in THF (40 mL, 80 mmol). A suspension formed after stirring for a few minutes. The reaction mixture was left at RT overnight and then the solid was filtered off and discarded. The filtrate was concentrated under reduced pressure and the residue was partitioned between DCM and satd. sodium hydrogen carbonate solution (aq.). The organic layer was dried (Na2SO4) and evaporated to afford the title compound as a solid.

Workup

  1. customA suspension formed
  2. filtrationthe solid was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was partitioned between DCM
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-5431dfc55cb44a0b9fe7f0fef9ba29c6
Source dataset
uspto-grants-2010_12
Patent number
US07846955B2

Reaction notes

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