Hydrochloric Acid → HCID 69217980, compound

3-(4-Dimethylamino-4-phenyl-cyclohexyl)-acrylonitrile (400 mg, 1.57 mmole) was dissolved in methanol (25 ml). Nickel(II) chloride hexahydrate (747.6 mg, 3.14 mmole) was added to the solution. NaBH4 (594 mg, 15.7 mmole) was then added in portions with ice water cooling. A black precipitate was formed accompanied by evolution of hydrogen. Once addition was complete, stirring was continued at 20° C. for 1 h. Working up was performed by combining the reaction mixture with 1M hydrochloric acid (15 ml). The black precipitate was filtered out on Celite and thoroughly washed with 1M hydrochloric acid (3×7 ml). The hydrochloric, aqueous-methanolic solution was reduced to half its volume in order to remove the methanol. The remaining aqueous phase was extracted with ether (3×15 ml) to remove neutral substances. The batch was then alkalised (pH 11) by addition of 2M NaOH, resulting in the formation of a bulky precipitate which did not dissolve even on addition of EE. The precipitate was filtered out and washed with water (1×3 ml) and EE (3×5 ml). The two phases of the clear mother liquor were separated. The aqueous phase was extracted with EE (3×15 ml). The combined extracts were washed with NaCl-solution (2×10 ml), dried over sodium sulfate and the solvent removed by distillation. The resultant residue was the mixture of the diastereoisomers of [4-(3-aminopropyl)-1-phenylcyclohexyl]dimethylamine (203 mg, light yellow oil, 50%).

1. customA black precipitate was formed
2. additionOnce addition
3. filtrationThe black precipitate was filtered out on Celite
4. washthoroughly washed with 1M hydrochloric acid (3×7 ml)
5. customto remove the methanol
6. extractionThe remaining aqueous phase was extracted with ether (3×15 ml)
7. customto remove neutral substances
8. additionby addition of 2M NaOH
9. customresulting in the formation of a bulky precipitate which
10. dissolutiondid not dissolve even on addition of EE
11. filtrationThe precipitate was filtered out
12. washwashed with water (1×3 ml) and EE (3×5 ml)
13. customThe two phases of the clear mother liquor were separated
14. extractionThe aqueous phase was extracted with EE (3×15 ml)
15. washThe combined extracts were washed with NaCl-solution (2×10 ml)
16. dry with materialdried over sodium sulfate
17. customthe solvent removed by distillation
18. additionthe mixture of the diastereoisomers of [4-(3-aminopropyl)-1-phenylcyclohexyl]dimethylamine (203 mg, light yellow oil, 50%)

ORD record

ord-e9b667a54f6a4205aefbebff7d5d1c06

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07348354B2