1,2-Dichloroethane → HCID 66716829, compound

HRID 1184434Notes

Reaction equation

HRID 1184434 reaction equation
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([C:12]([OH:14])=O)=[CH:11][C:4]=2[NH:3]1.[C:15]1([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:15]1([CH:21]2[CH2:22][CH2:23][N:24]([C:12]([C:10]3[CH:9]=[CH:8][C:5]4[O:6][CH2:7][C:2](=[O:1])[NH:3][C:4]=4[CH:11]=3)=[O:14])[CH2:25][CH2:26]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 698734-PhenylpiperidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7061213-Oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylic acid

Product 1

HCID 66716829HCID 66716829, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 104 (0.5 mmol) in DMF (4 mL) was added 4-phenylpiperidine (0.75 mmol), EDC (0.6 mmol), and HOBt (0.6 mmol) followed by Hunig's base (1.5 mmol). The solution was stirred at 23° C. for 4 h and then water (15 mL) was added. The resulting solid was isolated by filtration, washed with water and dried in vacuo to give a white solid: 1H NMR (DMSO-d6, 400 MHz): δ=10.81 (s, 1H), 7.24-7.32 (m, 5H), 7.20 (t, J=6.9 Hz, 1H), 7.01 (d, J=1.5 Hz, 1H), 6.98 (d, J=10.9 Hz, 3H), 4.62 (s, 2H), 3.90 (s, 0H), 3.33 (s, 0H), 2.81 (t, J=12.0 Hz, 1H), 1.73-1.85 (m, 2 H), 1.59 ppm (dd, J=12.5, 3.7 Hz, 2H). ESI-MS: m/z 337.2 (M+H)+.

Workup

  1. customThe resulting solid was isolated by filtration
  2. washwashed with water
  3. customdried in vacuo
  4. customto give a white solid

Sources & evidence

ORD record
ord-7ad602e365934fc9b3fd991bc0639973
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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