Triethylamine → HCID 42599944, compound

HRID 1362568Notes

Reaction equation

HRID 1362568 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[O:2].C1(/C=[CH:20]/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])C=CC=CC=1.[CH2:26](N(CC)CC)C.[C:33]1(/[CH:39]=[C:40](\C)/[CH:41]=[CH:42]/C(Cl)=O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[CH3:26][O:25][C:23](=[O:24])[CH2:22][CH2:21][CH2:20][CH2:11][CH2:12][NH:8][C:1](=[O:2])/[CH:42]=[CH:41]/[CH:40]=[CH:39]/[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 15495121552-94-9HCID 21265413HCID 21265413, compound

Product 1

HCID 42599944HCID 42599944, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Method J1A) 1,1′-Carbonyldiimidazole (0.36 g, 2.2 mmol) was added to a solution of 5-phenyl-penta-2E,4E-dienoic acid (1/1) (0.35 g, 2 mmol) in dry tetrahydrofuran (10 ml) and the obtained mixture was stirred for 1 hour at ambient temperature. To the mixture triethylamine (0.30 g 3.0 mmol) and methyl 6-aminohexanoate hydrochloride (2c) (0.40 g, 2.2 mmol) were added and the resultant suspension was stirred for 6 hours at ambient temperature. The solvent was removed under reduced pressure, to the residue water (15 ml) was added and the precipitate was filtered off, washed with water and dried. The title compound (0.36 g, 60%) was obtained as a white solid. M.p. 125-127° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.05-1.72 (6H, m, CH2); 2.29 (2H, t, J=7.3 Hz, CH2); 3.12 (2H, q, J=6.0 Hz, CH2H); 3.58 (3H, s, CH3); 6.12 (1H, d, J=14.8 Hz, CH); 6.91-7.16 (2H, m, CH—CH); 7.23-7.66 (6H, m, C6H5, CH); 8.05 (1H, t, J=5.8 Hz, NH).

Workup

  1. customThe solvent was removed under reduced pressure, to the residue water (15 ml)
  2. additionwas added
  3. filtrationthe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-fa5586cf11354a7f8c903c1bd46bb713
Source dataset
uspto-grants-2011_02
Patent number
US07880020B2

Reaction notes

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