Cyclopropylamine → Decylamine

To a solution of N-(4-chloro-3-formylbenzyl)-N-methylacetamide from the previous step (1 eq.) in THF (0.08 M) was added cyclopropylamine (2 eq.) and freshly activated 3A molecular sieves. The resulting mixture was stirred at RT for 48 h. The molecular sieves were then filtered off and the filtrate was evaporated in vacuo. The resulting residue was taken up in methanol (0.07 M) and added sodium borohydride (2 eq.). After 2 h of stirring at RT, the reaction was quenched by the addition of 1 N aq. HCl. The volatiles were removed in vacuo and the resulting residue was partitioned between EtOAc and H2O. The organic layer was separated and the aqueous layer was back extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a colorless oil.

1. filtrationThe molecular sieves were then filtered off
2. customthe filtrate was evaporated in vacuo
3. stirringAfter 2 h of stirring at RT
4. customthe reaction was quenched by the addition of 1 N aq. HCl
5. customThe volatiles were removed in vacuo
6. customthe resulting residue was partitioned between EtOAc and H2O
7. customThe organic layer was separated
8. extractionthe aqueous layer was back extracted with EtOAc
9. washThe combined organic extracts were washed with brine
10. dry with materialdried over Na2SO4
11. filtrationfiltered

ORD record

ord-92de172b34514d39b3dae81bc2c4003f

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2