Diisopropylethylamine → HCID 67168960, compound

HRID 2170867Notes

Reaction equation

HRID 2170867 reaction equation
Cl.[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[CH3:16][O:17][C:18]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](O)=[O:24])=[O:19].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([C:23]([C:22]3[CH:21]=[C:20]([CH:28]=[CH:27][CH:26]=3)[C:18]([O:17][CH3:16])=[O:19])=[O:24])[CH2:12][CH2:13]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 177497914-(4-Chlorophenoxy)piperidine hydrochloride

Product 1

HCID 67168960HCID 67168960, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-(4-chlorophenoxy)piperidine hydrochloride (200 mg, 0.81 mmol), 3-(methoxycarbonyl)benzoic acid (145 mg, 0.81 mmol), and N,N-diisopropylethylamine (0.56 mL, 3.22 mmol) in N,N-dimethylformamide (4 mL) was add HBTU (458 mg, 1.21 mmol) at room temperature. After stirring at 60° C. for 2 hours, the mixture was poured into water (20 mL). This was extracted with ethyl acetate (20 mL) and washed with water (20 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate) to give 301 mg (>99% yield) of the title compound as yellow syrup.

Workup

  1. extractionThis was extracted with ethyl acetate (20 mL)
  2. washwashed with water (20 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate)

Sources & evidence

ORD record
ord-5b6944052a6f4cc08bb240aa5d80d975
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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