Potassium Carbonate → N-[3-{4-(diphenylmethyl)hexahydro-1H-1,4-diazepin-1-yl}propyl]phthalimide

HRID 365096Notes

Reaction equation

[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:22][CH2:23][CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:15]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:14][CH2:13][CH2:12][N:11]([CH2:22][CH2:23][CH2:24][N:25]3[C:29](=[O:30])[C:28]4=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]4[C:26]3=[O:35])[CH2:10][CH2:9]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 1-(diphenylmethyl)hexahydro-1H-1,4-diazepine (2.0 g), N-(3-bromopropyl)phthalimide (2.01 g) and anhydrous potassium carbonate (3.1 g) was added acetone (10 ml) and then stirred for 6 hours at 50° C. The reaction mixture was filtered and the filtrate was concentrated in vacuo and then the resultant oily residue was subjected to a column chromatography on silica gel using a mixture of ethyl acetate and chloroform (2:3) for elution to give N-[3-{4-(diphenylmethyl)hexahydro-1H-1,4-diazepin-1-yl}propyl]phthalimide (2.2 g) as an oil.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated in vacuo
additiona mixture of ethyl acetate and chloroform (2:3)
washfor elution

Sources & evidence

ORD record: ord-8f516d2484194c28a8790494e2e63171
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04608375

Reaction notes

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