Malic Acid → HCID 59752657, compound

HRID 2106213Notes

Reaction equation

HRID 2106213 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[N+]([CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([O-])=O.C(O)(=O)C(CC(O)=O)O>CCOC(C)=O>[CH2:11]([N:18]1[C:7]2[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][C:6]=2[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:22]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 525Malic AcidHCID 7504BenzylamineHCID 7626Beta-NitrostyreneHCID 793131-(Isopropyl)-4-piperidone

Product 1

HCID 59752657HCID 59752657, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound (111.0 mg) was prepared from 372 μL of 1-isopropyl-piperidin-4-one, 270 μL of benzylamine, and 0.38 g of (2-nitro-vinyl)-benzene as in Example 41. The product was diluted with EtOAc and malic acid (39.0 mg) was added. The solids that formed were collected by filtration to give the title compound as a maleate salt. MS (ESI): exact mass calculated for C23H26N2, 330.21; found, m/z 331.2 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.38-7.33 (m, 6H), 7.30-7.27 (m, 1H), 7.23-7.19 (m, 3H), 7.14 (s, 1H), 6.25 (s, 2H), 5.15 (s, 2H), 3.74-3.66 (m, 1H), 2.96-2.91 (br m, 2H), 1.41 (d, J=6.6 Hz, 6H).

Workup

  1. additionwas added
  2. customThe solids that formed
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-da56daf4db104b84807f94c1cec9b8a4
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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