Bis(2-Methoxyethyl)amine → HCID 16049333, compound

HRID 1873498Notes

Reaction equation

HRID 1873498 reaction equation
C[Al](C)C.[CH3:5][O:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][O:12][CH3:13].[NH2:14][C:15]1[CH2:16][C:17]([C:33](OCC)=[O:34])=[CH:18][C:19]2[CH:25]=[CH:24][C:23]([C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])=[CH:22][C:20]=2[N:21]=1>C1(C)C=CC=CC=1.ClCCCl>[NH2:14][C:15]1[CH2:16][C:17]([C:33]([N:9]([CH2:10][CH2:11][O:12][CH3:13])[CH2:8][CH2:7][O:6][CH3:5])=[O:34])=[CH:18][C:19]2[CH:25]=[CH:24][C:23]([C:26]([F:32])([F:31])[C:27]([F:28])([F:29])[F:30])=[CH:22][C:20]=2[N:21]=1

Participants

6

Reactant 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 15953875Ethyl 2-amino-8-(pentafluoroethyl)-3H-1-benzazepine-4-carboxylateHCID 16682925Trimethylaluminum

Product 1

HCID 16049333HCID 16049333, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

Trimethylaluminum (0.34 mL of a 2.0 M solution in toluene) was added to bis(2-methoxyethyl)amine (92 mg, 0.69 mmol) in DCE (3 mL). After 10 minutes solid (1E,4E)-ethyl 2-amino-8-(perfluoroethyl)-3H-benzo[b]azepine-4-carboxylate (80 mg, 0.23 mmol) was added and the vessel was sealed and heated to 75° C. for 16-20 hours. Upon cooling the reaction was quenched with saturated Rochelle's salt (2 mL) and after 20 minutes the mixture was partitioned between CH2Cl2 (50 mL) and brine (50 mL). The phases were separated and the aqueous was extracted with CH2Cl2 (2×20 mL). The combined organics were dried and concentrated. The crude material was purified via preparative TLC (2, 0.5 mm plates, eluting with 5-10% MeOH/CH2Cl2 with 4-6 drops of NH4OH). 1H NMR (CDCl3) δ 2.81 (s, 2H), 3.36 (s, 6H), 3.55-3.74 (m, 8H), 6.98 (s, 1H), 7.20 (d, 1H), 7.40 (d, 1H), 7.39 (s, 1H).

Workup

  1. customthe vessel was sealed
  2. temperatureUpon cooling the reaction
  3. customwas quenched with saturated Rochelle's salt (2 mL) and after 20 minutes the mixture
  4. customwas partitioned between CH2Cl2 (50 mL) and brine (50 mL)
  5. customThe phases were separated
  6. extractionthe aqueous was extracted with CH2Cl2 (2×20 mL)
  7. customThe combined organics were dried
  8. concentrationconcentrated
  9. customThe crude material was purified via preparative TLC (2, 0.5 mm plates, eluting with 5-10% MeOH/CH2Cl2 with 4-6 drops of NH4OH)

Sources & evidence

ORD record
ord-3a197551a0b84641bad55dfaf0acf128
Source dataset
uspto-grants-2012_11
Patent number
US08304407B2

Reaction notes

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