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

HRID 1505152

Reaction equation

HRID 1505152 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-897c6a7cbf9c4d42a87e041825ca2c9c
Source dataset
uspto-grants-2015_12
Patent number
US09216971B2

Linked notes

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