Dimethylformamide → 11-{1-[2-(Phenyl)ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine oxalate

HRID 365137

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]2[C:13]3=[CH:14][CH:15]=[CH:16][N:12]3[CH2:11][C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]=3[O:8]2)[CH2:3][CH2:2]1.Br[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:30]([O-:33])([O-:32])=O.[K+].[K+].CN(C=[O:40])C>>[C:9]([OH:8])(=[O:40])[C:30]([OH:33])=[O:32].[C:24]1([CH2:23][CH2:22][N:1]2[CH2:2][CH2:3][CH:4]([CH:7]3[C:13]4=[CH:14][CH:15]=[CH:16][N:12]4[CH2:11][C:10]4[CH:17]=[CH:18][CH:19]=[CH:20][C:9]=4[O:8]3)[CH2:5][CH2:6]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 7666Phenethyl bromide

HCID 11430Potassium Carbonate

HCID 1368935811-(piperdin-4-yl)-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine

Product 1

HCID 2019167911-{1-[2-(Phenyl)ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine oxalate

Conditions

Temperature: 90 °C

Procedure

To 50 ml DMF were added 11-(piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine (4.5 g, 0.017 mole), (2-bromoethyl)-benzene (4.3 ml, 0.03 mole), milled K2CO3 (10.0 g, 0.07 mole) and KI (0.01 g). After stirring at 90° C. for four hours the mixture was cooled and filtered, and the filtrate was concentrated in vacuo to an oil. This oil was dissolved in ethyl acetate, washed twice with water and dried (saturated NaCl, anhydrous MgSO4).

Workup

temperaturewas cooled
filtrationfiltered
concentrationthe filtrate was concentrated in vacuo to an oil
dissolutionThis oil was dissolved in ethyl acetate
washwashed twice with water
dry with materialdried (saturated NaCl, anhydrous MgSO4)

Sources & evidence

ORD record: ord-4a0197bcf38041eaa9c2b2fbe18c0959
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04608374

Linked notes

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