Triethylamine → HCID 69100376, compound

HRID 2114994Notes

Reaction equation

HRID 2114994 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(N(CC)CC)C.[CH2:25]([CH:32]1[CH2:37][CH2:36][N:35]([C:38](=[O:42])[C:39](Cl)=[O:40])[CH2:34][CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)(Cl)Cl>[CH2:25]([CH:32]1[CH2:33][CH2:34][N:35]([C:38](=[O:42])[C:39]([NH:17][C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[NH:8][CH2:9][CH2:10]3)=[O:40])[CH2:36][CH2:37]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16110249HCID 16110249, compoundHCID 22240520tert-Butyl 5-amino-2,3-dihydro-1H-indole-1-carboxylate

Product 1

HCID 69100376HCID 69100376, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 0.5 g (2.25 mmol) of 5-amino-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester and 0.4 ml (2.8 mmol) of triethylamine in 20 ml of chloroform 0.7 g (2.6 mmol) of (4-benzyl-piperidin-1-yl)-oxo-acetyl chloride in 10 ml of chloroform is added dropwise at 0° C. The reaction mixture is stirred at room temperature for 1 hour, then washed with water and the organic layer is concentrated. The residue is purified by column chromatography using Kieselgel 60 (Merck) as adsorbent and toluene:methanol=4:1 as eluent to yield 0.9 g (88.7%) of the title compound as solid. The crude product is used in the next step.

Workup

  1. washwashed with water
  2. concentrationthe organic layer is concentrated
  3. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-85cb41dd1a4f4066bf5f8c89cc5b340a
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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