Triethylamine → HCID 86589864, compound

HRID 489893Notes

Reaction equation

HRID 489893 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15](Cl)=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.Cl.Cl.[CH2:20]([O:22][C:23]([CH:25]1[CH2:30][CH2:29][CH2:28][N:27]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:26]1)=[O:24])[CH3:21].C(N(CC)CC)C.[OH-].[Na+]>ClCCl>[CH2:20]([O:22][C:23]([C@@H:25]1[CH2:30][CH2:29][CH2:28][N:27]([CH:31]2[CH2:32][CH2:33][N:34]([C:15]([C:13]3[C:14]4[C:5]([CH:6]=[C:7]5[C:12]=3[CH:11]=[CH:10][CH:9]=[CH:8]5)=[CH:4][CH:3]=[CH:2][CH:1]=4)=[O:16])[CH2:35][CH2:36]2)[CH2:26]1)=[O:24])[CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 167528Anthracene-9-carbonyl chlorideHCID 44891098HCID 44891098, compound

Product 1

HCID 86589864HCID 86589864, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Anthracene-9-carbonyl chloride (62.2 mmol) was suspended in anhydrous dichloromethane (30 mL) and added slowly by pipette to a solution of [1,4′]bipiperidinyl-3-Carboxylic acid ethyl ester bishydrochloride (62.2 mmol) and triethylamine (4 eq., 35 mL) in anhydrous dichloromethane (50 mL) at such a rate that a gentle reflux was maintained. The resulting suspension was stirred overnight at ambient temperature then shaken with ice-cold water containing sodium hydroxide (0.19 mol, 7.6 g). The dichloromethane layer was separated and the aqueous layer was extracted with dichloromethane. The combined dichloromethane solution was washed with water, dried with anhydrous sodium sulfate, diluted with a little xylene and evaporated to dryness to give the title compound (containing a small amount of the corresponding isopropyl ester) as a pale yellow gummy foam (30.8 g).

Workup

  1. temperaturea gentle reflux
  2. temperaturewas maintained
  3. stirringthen shaken with ice-cold water
  4. customThe dichloromethane layer was separated
  5. extractionthe aqueous layer was extracted with dichloromethane
  6. washThe combined dichloromethane solution was washed with water
  7. dry with materialdried with anhydrous sodium sulfate
  8. additiondiluted with a little xylene
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-4f757b0a0fcc477b89828ab6da0b1392
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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