4-Methylmorpholine → HCID 89726095, compound

HRID 592062Notes

Reaction equation

HRID 592062 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)=[O:2].[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([N:15]1[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]1)=[O:8])=[O:2]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 120773-CarboxybenzaldehydeHCID 143452tert-Butyl piperazine-1-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 89726095HCID 89726095, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-formylbenzoic acid (600 mg, 3.99 mmol) in DCM (12 mL) were added tert-butyl piperazine-1-carboxylate (818.8 mg, 4.40 mmol), HATU (1.82 g, 4.80 mmol), NMM (1.1 mL, 9.99 mmol), and DMAP (49 mg, 0.39 mmol) at 0° C. Reaction was stirred at RT for 16 h. TLC analysis indicated complete consumption of starting material. The reaction mixture was diluted with DCM and washed with water. Organic layer was separated and dried over Na2SO4 and concentrated. Column chromatography of crude material afforded pure product tert-butyl 4-(3-formylbenzoyl)piperazine-1-carboxylate as off-white solid (990 mg, 78%).

Workup

  1. customReaction
  2. customconsumption of starting material
  3. additionThe reaction mixture was diluted with DCM
  4. washwashed with water
  5. customOrganic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c9e60487e3cf40a290e1d69ecc79b01d
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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