Hydrochloric Acid → rac-Atomoxetine EP Impurity C
Reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([OH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>>[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH3:5])=[CH:7][CH:8]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1Participants
Procedure
Under stirring, while maintaining the temperature between about 15° and about 25° C. with an ice-water bath, 14.25 g of 36 percent aqueous hydrogen chloride are dropped on the filtered organic phase. 4-ATM Hydrochloride (mw 291.82) crystallizes in bulk, and 40 ml of n-butyl acetate are added to allow stirring. The resulting suspension is stirred at about 20° C. for 1 hour, the solid is collected by filtration, washed twice with 40 ml of n-butyl acetate, and dried for 18 hours under vacuum at about 50° to about 60° C., yielding 23.5 g of product, having a melting point of about 164° to about 167° C., for a 33 percent yield, based on the N-methyl-3-hydroxy-3-phenylpropylamine starting material. The 4-ATM HCl is found by chiral HPLC as a mixture of enantiomers, with a relative ratio of 58:42.
Sources & evidence
- ORD record
- ord-1c03530d2f3947fbbe4b3b0df1a11a0b
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07378553B2
Reaction notes
Loading…