Triethylamine → HCID 18918517, compound

HRID 864782Notes

Reaction equation

HRID 864782 reaction equation
Cl.Cl.[N:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH2:19](N(CC)CC)[CH3:20].C1C=CC2N(O)N=NC=2C=1.C(N=C=NC(C)C)(C)C.C([N:47]1[CH2:52][CH2:51][CH:50]([CH2:53][C:54]([OH:56])=[O:55])[CH2:49][CH2:48]1)C>CN(C)C=O>[N:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]([N:47]3[CH2:48][CH2:49][CH:50]([CH2:53][C:54]([O:56][CH2:19][CH3:20])=[O:55])[CH2:51][CH2:52]3)=[O:18])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 18918276(1-Ethylpiperidin-4-yl)acetic acidHCID 189185271-Piperazineacetic acid, 4-(4-pyridinyl)-, hydrochloride (1:2)

Product 1

HCID 18918517HCID 18918517, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution containing 1-(4-pyridyl)-4-carboxymethylpiperazine dihydrochloride 1/4H2O(400 mg, 1.33 mMoles), triethylamine (0.4 ml, 2.66 mMoles) and HOBT (0.2 g, 1.46 mMoles) in dry dimethylformamide (20 ml) was treated with diisopropylcarbodiimide (0.23 ml, 1.46 mMoles) and the mixture was stirred for 5 minutes. Ethyl 4-carboxymethylpiperidine was added and the mixture was stirred for a further 4 hours. The mixture was concentrated to half volume under reduced pressure and then poured into water (50 ml) and extracted with ethyl acetate (3×20 ml) and dichloromethane (3×20 ml). The combined organic extracts were concentrated under reduced pressure and the residue was purified by chromatography (flash column made with grade III alumina and eluted with a gradient of 0-1% methanol in dichloromethane) to give the title compound (130 mg) as a colourless oil; NMR (d6DMSO): 0.9-1.1 (m,2H), 1.2 (t,3H), 1.65 (d,2H), 1.8-2.0 (m,1H), 2.2 (d,2H), 2.5 (m,2H), 2.9-3.4 (m,10H), 4.0 (q,2H+m,1H), 4.3 (d,1H), 6.8 (d,2H), 8.15 (d,2H); m/e 375 (M+H)+.

Workup

  1. stirringthe mixture was stirred for a further 4 hours
  2. concentrationThe mixture was concentrated to half volume under reduced pressure
  3. additionpoured into water (50 ml)
  4. extractionextracted with ethyl acetate (3×20 ml) and dichloromethane (3×20 ml)
  5. concentrationThe combined organic extracts were concentrated under reduced pressure
  6. customthe residue was purified by chromatography (flash column
  7. washeluted with a gradient of 0-1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-73cb8c9fe4dc46848a69624c10747b1e
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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