Potassium Carbonate → 2-allyl-8-(8-azidooctyloxy)-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one

HRID 1653869Notes

Reaction equation

[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:6]=2[C:5]1=[O:16])[CH:2]=[CH2:3].[N:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]OS(C1C(C)=CC=CC=1)(=O)=O)=[N+:18]=[N-:19].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:11]=[CH:12][C:13]([O:15][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][N:17]=[N+:18]=[N-:19])=[CH:14][C:6]=2[C:5]1=[O:16])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 65 °C

Procedure

A suspension of 2-allyl-8-hydroxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one (1.0 g, 0.0049 mol), 8-azido-1-(toluenesulfonyloxy)octane (1.50 g, 0.0049 mol) and K2CO3 in N,N-dimethylformamide (20 mL) was stirred vigorously under argon, and heated at 65° C. for 18 hours. The solution was then partitioned between ethyl acetate and brine, and the combined organic layers were washed with water, dried (K2CO3), filtered, and concentrated in vacuo. The residue was purified by chromatography over silica gel to yield 920 mg (51%) of 2-allyl-8-(8-azidooctyloxy)-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one as a colorless oil;

Workup

customThe solution was then partitioned between ethyl acetate and brine
washthe combined organic layers were washed with water
dry with materialdried (K2CO3)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by chromatography over silica gel

Sources & evidence

ORD record: ord-80de571b8f7d4fe2807b1878a1c6ecd1
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05403836

Reaction notes

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