Dimethylformamide → HCID 11979211, compound

HRID 657637Notes

Reaction equation

HRID 657637 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.CN(C)C=O.Cl[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH2:38][N:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)=[CH:31][CH:30]=2)=[CH:25][CH:24]=1>>[N:39]1([CH2:38][CH2:37][CH2:36][O:35][C:32]2[CH:33]=[CH:34][C:29]([C:26]3[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH2:20][CH2:19][N:7]4[CH2:12][CH2:11][O:10][CH2:9][CH2:8]4)=[CH:24][CH:25]=3)=[CH:30][CH:31]=2)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 23150304HCID 23150304, compound

Product 1

HCID 11979211HCID 11979211, compoundYield 22.1%

Procedure

A suspension of potassium carbonate (138 mg) in a mixture of 1-{3-[4′-(3-chloropropoxy)biphenyl-4-yloxy]propyl}piperidine (100 mg), morpholine (65 mg) and N,N-dimethylformamide (1 mL) is stirred for four days at room temperature. The mixture is filtered, concentrated under reduced pressure and purified by chromatography over silica gel with dichloromethane/methanol 82/2 as eluent. Fractions containing the expected product are pooled and concentrated under reduced pressure to give 25 mg of 4-(3-{[4′-(3-piperidinopropoxy)biphenyl-4-yl]oxy}propyl)morpholine as a off white solid which is salted with 9.4 mg of oxalic acid yielding 15 mg of 4-(3-{[4′-(3-piperidinopropoxy)biphenyl-4-yl]oxy}propyl)-morpholine, dioxalate as a white solid.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated under reduced pressure
  3. custompurified by chromatography over silica gel with dichloromethane/methanol 82/2 as eluent
  4. additionFractions containing the expected product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f432117650b64aa7a95257d8cda2f9a8
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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