Morpholine → 9-Anthryl[(3R)-3-(4-morpholinylcarbonyl)[1,4'-bipiperidin]-1'-yl]methanone

HRID 489895Notes

Reaction equation

HRID 489895 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]4[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]([OH:31])=O)[CH2:24]4)[CH2:19][CH2:18]2)=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.C(N(CC)CC)C>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1.ClCCl>[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]([N:17]2[CH2:18][CH2:19][CH:20]([N:23]4[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]([N:36]5[CH2:41][CH2:40][O:39][CH2:38][CH2:37]5)=[O:31])[CH2:24]4)[CH2:21][CH2:22]2)=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 23589106HCID 23589106, compound

Product 1

HCID 4490979-Anthryl[(3R)-3-(4-morpholinylcarbonyl)[1,4'-bipiperidin]-1'-yl]methanone

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The crude (3R)-1′-(anthracene-9-carbonyl)-[1,4′]bipiperidinyl-3-carboxylic acid as prepared above (approx 22 mmol) was heated under reflux in a mixture of chloroform (75 mL, Aldrich, amylenes-stabilized) and thionyl chloride (10 mL, 0.137 mmol) until all the solid had dissolved. The mixture was diluted with toluene, evaporated to dryness under vacuum and anhydrous dichloromethane (40 mL) added. A mixture of morpholine (21 mmol, 1.81 mL) and triethylamine (62 mmol, 8.7 mL) in anhydrous dichloromethane (40 mL) was added and the solution was stirred for 16 hr at ambient temperature. The mixture was washed with ice-cold 0.1M sodium hydroxide solution, dried over anhydrous sodium sulfate, diluted with toluene and evaporated to dryness. The residue was purified by chromatography on 240 g silica gel eluting with a 4%-7%-10% methanol-dichloromethane gradient to give the title compound as a pale yellow glassy foam.

Workup

  1. temperaturewas heated
  2. dissolutionhad dissolved
  3. customevaporated to dryness under vacuum and anhydrous dichloromethane (40 mL)
  4. additionadded
  5. additionwas added
  6. washThe mixture was washed with ice-cold 0.1M sodium hydroxide solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. additiondiluted with toluene
  9. customevaporated to dryness
  10. customThe residue was purified by chromatography on 240 g silica gel eluting with a 4%-7%-10% methanol-dichloromethane gradient

Sources & evidence

ORD record
ord-b2a8817c47a14cb79288ce6ca561af77
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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