Malic Acid → HCID 59752657, compound

HRID 599904Notes

Reaction equation

HRID 599904 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-2c577c10367f4257a8952219893f93c0
Source dataset
uspto-grants-2011_03
Patent number
US07897771B2

Reaction notes

Loading…