Triethylamine → HCID 57698131, compound

HRID 1504101Notes

Reaction equation

HRID 1504101 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.C(N(CC)CC)C.Br[CH2:24][CH2:25][O:26][CH2:27][CH2:28]Br>CN(C=O)C.C(OCC)(=O)C>[N:1]1([CH:2]2[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21521Bis(2-bromoethyl) etherHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamate

Product 1

HCID 57698131HCID 57698131, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of tert-butyl N-(4-aminocyclohexyl)carbamate (1.07 g, 4.99 mmol, 1.00 equiv) in DMF (10 mL) was added triethylamine (1.26 g, 12.48 mmol, 2.50 equiv) and 1-bromo-2-(2-bromoethoxy)ethane (1.4 g, 6.04 mmol, 1.20 equiv). The resulting solution was stirred overnight at 70° C. The resulting solution was diluted with ethyl acetate (100 mL), washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give 1.2 g (crude) of tert-butyl N-[4-(morpholin-4-yl)cyclohexyl]carbamate as a light yellow solid. MS (ES): m/z 285 (M+H)+.

Workup

  1. washwashed with brine (100 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-32afac3f7843496a8ef9c5a88d1eb8b5
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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