Dichloromethane → (4-Dimethylaminopiperidin-1-yl)(9H-xanthen-9-yl)methanone

HRID 220333

Reaction equation

HRID 220333 reaction equation
[CH:1]1[C:14]2[CH:13]([C:15]([OH:17])=O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.[CH3:21][N:22]([CH3:29])[CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>>[CH3:21][N:22]([CH3:29])[CH:23]1[CH2:28][CH2:27][N:26]([C:15]([CH:13]2[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[O:6][C:7]3[C:12]2=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:17])[CH2:25][CH2:24]1

Participants

7

Reactant 6

HCID 6344DichloromethaneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 65736Xanthene-9-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 417391N,N-Dimethylpiperidin-4-amine

Product 1

HCID 59828537(4-Dimethylaminopiperidin-1-yl)(9H-xanthen-9-yl)methanoneYield 90.4%

Procedure

To a stirred solution of 9H-xanthene-9-carboxylic acid (4.4 g, 19.4 mmol) in DCM (200 mL, 3 mol) was added dimethylpiperidin-4-yl-amine (2.5 g, 19.4 mmol). DIPEA (6.8 mL, 38.9 mmol) and HOBt (4.6 g, 34 mmol) were added to the mixture, followed by EDCI (4.5 g, 23.3 mmol). The mixture was stirred for 12 hours, then washed with water (300 mL), NaCl (sat.) (300 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure, and the crude material was purified via silica gel chromatography (10% MeOH/DCM w/1% NH3 (aq)) to yield the title compound (5.9 g).

Workup

  1. washwashed with water (300 mL), NaCl (sat.) (300 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. customthe crude material was purified via silica gel chromatography (10% MeOH/DCM w/1% NH3 (aq))

Sources & evidence

ORD record
ord-3ff150d2f0874a4db8b1542384e93d49
Source dataset
uspto-grants-2012_06
Patent number
US08202891B2

Linked notes

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