Oxalic Acid → HCID 15940927, compound

HRID 657671Notes

Reaction equation

HRID 657671 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[BH4-].[Na+].C(O)(=O)C(O)=O>CO.C(O)C>[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 4311764Sodium borohydrideHCID 23150285HCID 23150285, compound

Product 1

HCID 15940927HCID 15940927, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

To a solution of 1-{3-[4-(4-oxocyclohexyl)phenoxy]propyl}piperidine (250 mg) in methanol (3 mL) is added sodium borohydride (15 mg). The mixture is stirred for two days at room temperature, then concentrated under reduced pressure and purified by column chromatography on silica gel (eluent dichloromethane/methanol/ammonia from 99.5/0.5/0.05 to 99/1/0.1) to give 179 mg of crude base which is dissolved in ethanol (2 mL). A solution of oxalic acid (50 g) in ethanol (1 mL) is added. A white precipitate appears which is filtered, rinsed with diethyl ether and dried under reduced pressure to give 127 mg of 1-{3-[4-(4-hydroxycyclohexyl)phenoxy]propyl}piperidine as a white solid

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by column chromatography on silica gel (eluent dichloromethane/methanol/ammonia from 99.5/0.5/0.05 to 99/1/0.1)
  3. customto give 179 mg of crude base which
  4. filtrationis filtered
  5. washrinsed with diethyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-53b67daa4d0d4f3d9c225e264e9c4836
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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