Hydrochloric Acid → HCID 67314829, compound

HRID 1012588Notes

Reaction equation

[C:1]([O:4][CH2:5][CH2:6][N:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]=CC2C=CC=CC=2)=[CH:22][CH:21]=1)[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])(=[O:3])[CH3:2].Cl>C(O)C>[C:1]([O:4][CH2:5][CH2:6][N:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][CH:21]=1)[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH3:15])[CH2:16][CH2:17][CH3:18])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

118.4 g (259 mmol, 1.0 equivalent) of {[4-(benzylidene)aminomethylbenzyl]-(4-dipropylaminobutyl)amino}ethyl acetate (8a) and 900 ml of ethanol were charged in a 3-liter four-necked flask and cooled to 0° C. The mixture was added dropwise with 870 ml (2.59 mol, 10 equivalents) of 3N hydrochloric acid over 2.5 hours and stirred at 0° C. for one hour and at 25° C. for 18 hours. About 5% of the raw material (8a) remained as a result of confirmation by HPLC. Therefore, the reaction solution was added with 110 ml of 2N hydrochloric acid at 25° C. After three hours, the content of the raw material (8a) was measured by HPLC, and it was confirmed that the content decreased to 1% or less.

Workup

customa result of confirmation by HPLC
waitAfter three hours

Sources & evidence

ORD record: ord-489ded5bb3f54487ac808c40e64776f2
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977512B2

Reaction notes

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