Triethylamine → HCID 178453985, compound

HRID 1398082Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.Br[CH2:17][CH2:18][O:19][CH2:20][CH2:21]Br.C(N(CC)CC)C>CN(C)C=O>[N:1]1([C@H:2]2[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 21.43 g (0.1 mol) of tert-butyl N-(trans-4-aminocyclohexyl)carbamate in 250 mL of N,N-dimethylformamide were added 16.76 mL (0.12 mol) of bis(2-bromoethyl)ether and 34.85 mL (0.25 mol) of triethylamine, and the mixture was stirred for 6 hours at 70° C. Then solvent was removed under reduced pressure and the residue was treated with ethyl acetate. The organic layer was washed with sodium carbonate aqueous solution and saturated saline solution, then, dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: chloroform alone to chloroform/methanol=30/1) to give 19.92 g (70%) of the title compound.

Workup

customThen solvent was removed under reduced pressure
additionthe residue was treated with ethyl acetate
washThe organic layer was washed with sodium carbonate aqueous solution and saturated saline solution
dry with materialdried over with anhydrous sodium sulfate
customThe solvent was removed under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record: ord-bb8fb3002667436cb2f78bd65119d14e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901315B2

Reaction notes

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