Triethylamine → 1-(2-Azido-ethyl)-3-ethyl-3-(3-methoxy-phenyl)-azepan-2-one

HRID 1594906Notes

Reaction equation

HRID 1594906 reaction equation
[CH2:1]([C:3]1([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:10][CH2:11]O)[C:4]1=[O:13])[CH3:2].CCN(CC)CC.CS(Cl)(=O)=O.[N-:34]=[N+:35]=[N-:36].[Na+]>C(Cl)Cl.CN(C=O)C>[N:34]([CH2:11][CH2:10][N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C:3]([CH2:1][CH3:2])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[C:4]1=[O:13])=[N+:35]=[N-:36]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 217061943-Ethyl-1-(2-hydroxy-ethyl)-3-(3-methoxy-phenyl)-azepan-2-one

Product 1

HCID 217062381-(2-Azido-ethyl)-3-ethyl-3-(3-methoxy-phenyl)-azepan-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-ethyl-1-(2-hydroxy-ethyl)-3-(3-methoxyphenyl)-azepan-2-one (as described above in Step A) (0.6 g, 2.05 mmol) in CH2Cl2 (15 mL) at 0° C. was added NEt3 (0.85 mL, 6.15 mmol) and methanesulfonyl chloride (0.19 mL, 2.45 mmol). The mixture was stirred for 30 min at 25° C. then NaN3 (0.27 g, 4.1 mmol) in DMF (3 mL) was added. The reaction was stirred for 18 hr then partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with brine and dried (MgSO4) Filtration and concentration to dryness gave the title compound.

Workup

  1. stirringThe reaction was stirred for 18 hr
  2. customthen partitioned between EtOAc and saturated NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. customdried
  5. filtration(MgSO4) Filtration and concentration to dryness

Sources & evidence

ORD record
ord-52aac889810648f7b34a62fd033f6f67
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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