Ammonium Hydroxide → 5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine

HRID 2068562Notes

Reaction equation

Cl.Cl.[CH:3]1[N:7]2[C:8]3[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=3[CH2:10][CH2:11][CH:12]([NH2:13])[C:6]2=[N:5][CH:4]=1.[NH4+].[OH-]>O>[CH:3]1[N:7]2[C:8]3[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=3[CH2:10][CH2:11][CH:12]([NH2:13])[C:6]2=[N:5][CH:4]=1

Participants

Conditions

Temperature: 5 °C

Procedure

Charge a reactor with 35.9 kg of 5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine dihydrochloride and 453 ml of water. Add 29.7 L of NH4OH 25% slowly within 30 minutes maintaining the temperature below 25° C. After the addition, the pH is 9 and is a clear brown solution. Crystallization is induced by adding 31.5 grams of seeds at 22° C. Stir the suspension for 8 hrs and cool to 5° C. Filter and wash the filter cake with 54 L of cold water and dry the resulting filter cake in the filter using N2/vacuum for 31 hrs which yields 5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine. Dissolve 29 kg of the crude filter cake in 145 L of ethanol portionwise. Remove 73 L of solvent by vacuum distillation. Add 108 L of ethanol and remove and distillation 133 L of solvent until the final concentration is 2 L/kg. Perform an in-process Karl Fischer analysis to determine the final water content at ≦0.1% w/w.

Workup

temperaturemaintaining the temperature below 25° C
additionAfter the addition
customCrystallization
additionby adding 31.5 grams of seeds at 22° C
filtrationFilter
washwash the filter cake with 54 L of cold water
customdry the resulting
filtrationfilter cake in the filter
customfor 31 hrs

Sources & evidence

ORD record: ord-1a4cd79bd27046a9b62dd16feb3dd864
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299061B2

Reaction notes

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