Iem 2115 → Trans-1-ethyl-4-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)amino]-3-pyrrolidinol (Z)-Butenedioate

HRID 126923Notes

Reaction equation

[NH2:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.[CH2:17]([N:19]1[CH2:23][CH:22]2[O:24][CH:21]2[CH2:20]1)[CH3:18].[C:25]([O-:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([O-:30])=[O:29]>Cl>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29].[CH2:17]([N:19]1[CH2:23][C@@H:22]([NH:1][CH:2]2[C:3]3[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=3[CH2:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)[C@H:21]([OH:24])[CH2:20]1)[CH3:18]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 7.5 g (0.036 mole) of 5-amino-10,11-dihydro-5H-dibenzo[a,d]cycloheptene, 4.1 g (0.036 mole) of n-ethyl-3,4-epoxypyrrolidine and 2 drops concentrated hydrochloric acid was heated at 140° C. under a nitrogen atmosphere overnight. The residue was converted to the maleate. The salt was recrystallized twice from isopropyl alcohol, converted to the base, reconverted to the maleate, and recrystallized from isopropyl alcohol to yield 1.4 g. (7%) of white solid, m.p. 132°-135° C.

Workup

customThe salt was recrystallized twice from isopropyl alcohol
customrecrystallized from isopropyl alcohol
customto yield 1.4 g

Sources & evidence

ORD record: ord-c7a9b1408ab8447a96ede91574336901
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04254135

Reaction notes

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