4-Methylmorpholine → HCID 178420112, compound

HRID 1823929Notes

Reaction equation

HRID 1823929 reaction equation
C(OC([N:8]1[CH:17]([C:18](O)=O)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.[NH2:21][CH2:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=O.O[N:32]1C2C=CC=CC=2N=N1.CN(C)CCCCN=C=NCC.CN1CCOCC1>ClCCl>[C:25]1([C:23]2[N:32]=[C:18]([CH:17]3[CH2:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH2:9][NH:8]3)[NH:21][CH:22]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 11952PhenacylamineHCID 757711-HydroxybenzotriazoleHCID 27356492-[(Tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 21914090(4-Dimethylamino-butyl)-ethyl-carbodiimide

Product 1

HCID 178420112HCID 178420112, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3,4-Dihydro-1H-isoquinoline-2,3-dicarboxylic acid-2-tertbutyl ester (2.77 g, 10 mmol) and 2-amino-1phenyl-ethanone (1.71 g, 10 mmol), and HOBT (1-hydroxybenzo-triazole) (2.70 g, 20 mmol) were dissolved in dichloromethane (100 ml). The solution was cooled to 0° C. and then (4-dimethylamino-butyl)-ethyl-carbodiimide (2.29 g, 12 mmol) was added followed by NMM (N-methyl-morpholine) (1.31 g, 13 mmol). The reaction mixture was then warmed to room temperature. After 72 hours the reaction mixture was extracted with water, and the organic phase extracted consecutively with saturated NaHCO3, 2N citric acid and NaHCO3, dried over MgSO4, filtered and concentrated to yield the title product as a yellow foam. Liquid chromatography (LC) indicated the compound was 86% pure (214 nm), and was used without further purification.

Workup

  1. temperatureThe reaction mixture was then warmed to room temperature
  2. extractionAfter 72 hours the reaction mixture was extracted with water
  3. extractionthe organic phase extracted consecutively with saturated NaHCO3, 2N citric acid and NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0c88f47a4e4f4a6993f973cbcac9c7ef
Source dataset
uspto-grants-2006_05
Patent number
US07041681B2

Reaction notes

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