Oxalic Acid → (E)-3-(3-(2-(2,6,6-Trimethylcyclohex-1-enyl)vinyl)phenyl)propan-1-amine oxalate salt

HRID 628606Notes

Reaction equation

HRID 628606 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12]1[CH:13]=[C:14]([CH2:18][CH2:19][CH2:20][NH2:21])[CH:15]=[CH:16][CH:17]=1.[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24]>C(O)C>[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24].[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[C:12]1[CH:13]=[C:14]([CH2:18][CH2:19][CH2:20][NH2:21])[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 25101342(E)-3-(3-(2-(2,6,6-Trimethylcyclohex-1-enyl)vinyl)phenyl)propan-1-amine

Product 1

HCID 68943361(E)-3-(3-(2-(2,6,6-Trimethylcyclohex-1-enyl)vinyl)phenyl)propan-1-amine oxalate saltYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Example 22 was further purified by conversion to the oxalate salt using the following procedure: To a stirred solution of (E)-3-(3-(2-(2,6,6-Trimethylcyclohex-1-enyl)vinyl)phenyl)propan-1-amine (0.426 g, 1.50 mmol) in ethanol (3 mL) was added oxalic acid (2.0 mL, 20% solution in ethanol) at room temperature. After 30 min the suspension was filtered and the resulting solid dried to provide (E)-3-(3-(2-(2,6,6-Trimethylcyclohex-1-enyl)vinyl)phenyl)propan-1-amine oxalate salt as a white solid (0.433 g, 71%): 1H NMR (500 MHz, DMSO-d6) δ 7.31 (d, J=7.6 Hz, 2H), 7.26 (t, J=7.6 Hz, 1H), 7.07 (d, J=7.5 Hz, 1H), 6.72 (d, J=16.3 Hz, 1H), 6.32 (d, J=16.4 Hz, 1H), 2.79 (t, J=7.6 Hz, 2H), 2.64 (t, J=7.7 Hz, 2H), 2.02 (t, J=6.1 Hz, 2H), 1.86 (quint, J=7.7 Hz, 2H), 1.73 (s, 3H), 1.65-1.58 (m, 2H), 1.48-1.45 (m, 2H), 1.05 (s, 6H); 13C NMR (75 MHz, CD3OD) δ 164.2, 141.2, 137.6, 137.1, 132.4, 129.0, 128.7, 127.1, 126.9, 125.9, 123.7, 33.9, 32.4, 31.8, 28.8, 21.4, 18.7; ESI MS m/z 284 [M+H]+; HPLC (Method 2) 98.3% (AUC), tR=9.99 min. HRMS calcd for C20H29N [M+H]: 284.237. Found: 284.2364; Anal. Calcd for C20H29N.1.35C2H4O4: C, 67.32; H, 7.89; N, 3.46. Found: C, 67.31; H, 8.12; N, 3.47.

Workup

  1. customExample 22 was further purified by conversion to the oxalate salt using the following procedure
  2. filtrationAfter 30 min the suspension was filtered
  3. customthe resulting solid dried

Sources & evidence

ORD record
ord-6f1d6686d7ba45fd9b9ee2937a3b09a5
Source dataset
uspto-grants-2016_04
Patent number
US09314467B2

Reaction notes

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