Diisopropyl Ether → HCID 69904074, compound

HRID 2287537Notes

Reaction equation

HRID 2287537 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][NH:7][C@@H:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:5]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([O:23][C:24]([F:27])([F:26])[F:25])[CH:20]=[CH:19][C:18]=2[O:28][CH3:29])[CH2:4]1.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].O(C(C)C)C(C)C>CCO>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[OH:1][CH2:2][C@H:3]1[CH2:8][NH:7][C@@H:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@@H:5]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([O:23][C:24]([F:25])([F:26])[F:27])[CH:20]=[CH:19][C:18]=2[O:28][CH3:29])[CH2:4]1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 444972Fumaric AcidHCID 15454931HCID 15454931, compound

Product 1

HCID 69904074HCID 69904074, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of (2S*,3S*,5R*)-5-hydroxymethyl-3-[N-(2-methoxy-5-trifluoromethoxybenzyl)amino]-2-phenylpiperidine (0.298 g, 0.726 mmol) in EtOH (3.0 ml) was added fumaric acid (0.169 g, 1.45 mmol) in one portion. An additional volume of EtOH was added with heating at reflux, until the mixture became homogeneous. After the resultant pale yellow solution was allowed to cool to room temperature, (i-Pr)2O (2.0 ml) was added. After the mixture was left to stand in a refrigerator (at 4 C.) overnight, and then the precipitated white solids were collected by filtration, washed with (i-Pr)2O-i-PrOH, and dried in vacuo with heating at 50 C. to give title difumarete (0.382 g, 82.1%) as white powders. ##STR12## mp 162.0-165.0 C.; IRmax (nujol): 2565(br., s), 17179s), 1705(s), 1641(s), 1630(s), 1561(s), 1502(s), 1280(s), 1250(s), 1162(s), 973(s), 790(m), 751(s), 648(s) cm-1 ; 1H-NMR δ (DMSO-d6): 7.45-7.33(m, 4H), 7.22-7.12(m, 1H), 7.18-7.11(m, 2H), 6.91(d, J=8.8 Hz, 1H), 6.54(s, 4H), 4.29(br.s, 1H), 3.88-3.13(m, 13H), 3.56(s, 3H, 3.06-2.96(m, 1H), 2.90-2.83(m, 1H), 2.07-1.95(m, 1H), 1.93-1.80(m, 1H) ppm.

Workup

  1. temperaturewith heating
  2. temperatureat reflux, until the mixture
  3. waitAfter the mixture was left
  4. customto stand in a refrigerator (at 4 C.) overnight
  5. filtrationthe precipitated white solids were collected by filtration
  6. washwashed with (i-Pr)2O-i-PrOH
  7. customdried in vacuo
  8. temperaturewith heating at 50 C
  9. customto give title difumarete (0.382 g, 82.1%) as white powders

Sources & evidence

ORD record
ord-349b1b50261a49338a35cdf9f7371dfc
Source dataset
uspto-grants-2000_07
Patent number
US06083943

Reaction notes

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