Triethylamine → tert-butyl N-(2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)carbamate

HRID 647868Notes

Reaction equation

HRID 647868 reaction equation
[NH2:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13].[C:14]([O:18][C:19](ON=C(C1C=CC=CC=1)C#N)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C>O.O1CCOCC1>[C:14]([O:18][C:19]([NH:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13])=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 44344333-Amino-2,3,4,5-tetrahydro-1H-benzazepin-2-one

Product 1

HCID 13243501tert-butyl N-(2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-amino-2,3,4,5-tetrahydro-1H[1]benzazepin-2-one (4.0 g), 2-t-butyloxycarbonyloxyimino-2-phenylacetonitrile (6.1 g) and triethylamine (5 ml) in water (20 ml) and dioxane (25 ml) was stirred at room temperature for 18 hours. The resulting solid was filtered off and washed with water. Recrystallization from ethyl acetate gave 3-t-butyloxycarbonylamino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, m.p. 199°-201°.

Workup

  1. filtrationThe resulting solid was filtered off
  2. washwashed with water
  3. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-094ac74c660c422aadcfe28ba4a169be
Source dataset
uspto-grants-1983_10
Patent number
US04410520

Reaction notes

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