Triethylamine → HCID 42599944, compound

HRID 2100003Notes

Reaction equation

HRID 2100003 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′-Carbonyidiimidazole (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, CH2N); 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-b7db5936a93f485ba62d32ce07f0bc83
Source dataset
uspto-grants-2009_08
Patent number
US07569724B2

Reaction notes

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