Triethylamine → HCID 18918517, compound

HRID 1290479Notes

Reaction equation

HRID 1290479 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-be0a7dec23794f8ebc84c1a8a9159d6f
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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