1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874494, compound

HRID 1093804Notes

Reaction equation

HRID 1093804 reaction equation
CCN(C(C)C)C(C)C.[CH:10]1[C:22]2[NH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[C:12]([C:23]([OH:25])=O)[CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:48][CH2:49][C:50]([N:52]1[CH2:57][CH2:56][CH:55]([O:58][C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([C:65]([F:68])([F:67])[F:66])[CH:60]=2)[CH2:54][CH2:53]1)=[O:51]>CN(C=O)C.O>[O:51]=[C:50]([N:52]1[CH2:53][CH2:54][CH:55]([O:58][C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([C:65]([F:68])([F:66])[F:67])[CH:60]=2)[CH2:56][CH2:57]1)[CH2:49][NH:48][C:23]([C:12]1[CH:11]=[CH:10][C:22]2[NH:21][C:20]3[C:15]([C:14]=2[CH:13]=1)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:25]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 31520239H-Carbazole-3-carboxylic acidHCID 665915472-Amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride

Product 1

HCID 57874494HCID 57874494, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (137 mg, 1.0 mmol) was added to a stirred solution of to a stirred solution of 9H-carbazole-3-carboxylic acid (50 mg, 0.23 mmol) in DMF (4 mL) followed by HOBt (35 mg, 0.26 mmol) and EDCI (116 mg, 0.59 mmol). After 2 minutes, 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (88 mg, 0.26 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with cold water and the precipitate was filtered. The solid obtained was purified by recrystallisation from a mixture of 10% ethyl acetate in hexane and 50% MeOH in H2O to afford 81 mg (69.23% Yield) of 9H-carbazole-3-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 496, 91.03%. 1H NMR (300 MHz, DMSO-d6): δ 11.6 (s, 1H), 8.8 (s, 1H), 8.6 (t, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 7.6 (d, 2H), 7.46 (t, 1H), 7.36 (t, 2H), 7.24 (t, 1H), 4.9 (b, 1H), 4.3 (d, 3H), 4.0 (d, 2H), 3.5 (d, 2H), 2.1 (t, 2H), 1.7 (d, 2H).

Workup

  1. additionwas added
  2. filtrationthe precipitate was filtered
  3. customThe solid obtained
  4. customwas purified by recrystallisation from a mixture of 10% ethyl acetate in hexane and 50% MeOH in H2O

Sources & evidence

ORD record
ord-17bb03564de64a78a253b3422d00b469
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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