Methanol → HCID 20134489, compound

Under N2 atmosphere, 11 g of 4-amino-α-[(tert-butylamino)methyl]-3,5-dichlorobenzyl chloride is added to 75 ml of methanol at 0° C. After 20 minutes, the cooling bath is removed and the reaction mixture is stirred at ambient temperature. After the reaction is completed, the mixture is evaporated to dryness in vacuo. The residue is stirred in 75 ml of H2O and the mixture is made alkaline with 6 N NaOH solution and extracted with CH2Cl2 (3×50 ml). The organic phases are dried over MgSO4 and evaporated to dryness to afford an orange oil. This oil is dissolved in 150 ml of absolute EtOH and acidified with HCl/isopropyl alcohol solution to pH 2. The solution is evaporated to dryness and the residue is stirred in 75 ml of ethyl acetate. After cooling, this affords a pale yellow solid which is collected to give 6.97 g of the title compound, m.p. 195°-198° C. dec.

1. customthe cooling bath is removed
2. customthe mixture is evaporated to dryness in vacuo
3. stirringThe residue is stirred in 75 ml of H2O
4. extractionextracted with CH2Cl2 (3×50 ml)
5. dry with materialThe organic phases are dried over MgSO4
6. customevaporated to dryness
7. customto afford an orange oil
8. customThe solution is evaporated to dryness
9. stirringthe residue is stirred in 75 ml of ethyl acetate
10. temperatureAfter cooling
11. customthis affords a pale yellow solid which
12. customis collected

ORD record

ord-a38e9118e7714ca9b102a7bf4e292cb7

Source dataset

uspto-grants-1983_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04404222