Hydrochloric Acid → N-[4-(aminomethyl)cyclohexyl]-N-isopropylformamide

HRID 457687Notes

Reaction equation

HRID 457687 reaction equation
[O:1]1[CH2:6]COCC1.Cl.[CH:8]([C:11]([NH:13][CH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH:21]C(=O)OC(C)(C)C)[CH2:16][CH2:15]1)=O)(C)C.[CH3:29]COCC>>[NH2:21][CH2:20][CH:17]1[CH2:16][CH2:15][CH:14]([N:13]([CH:11]([CH3:8])[CH3:29])[CH:6]=[O:1])[CH2:19][CH2:18]1

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 22253966tert-butyl N-[4-(isopropylformylamino)cyclohexyl]methylcarbamate

Product 1

HCID 15896073N-[4-(aminomethyl)cyclohexyl]-N-isopropylformamideYield 100%

Procedure

Dioxane containing HCl was added (10 ml of 4N HCl solution) to the solution of tert-Butyl N-[4-(isopropylformylamino)cyclohexyl]methylcarbamate dissolved in 10 ml Et2O, stirred at room temperature for 2 hours, and the solvent removed to obtain N-[4-(aminomethyl)cyclohexyl]-N-isopropylformamide: 100% yield, 199 (ESMS, MH+); 1H NMR (CD3OD) δ 8.16 (s, 1H), 4.16 & 3.57 (two m, 1H), 3.70 (m, 1H), 2.79 (m, 2H), 1.36 (m, 6H), 1.91–1.06 (m, 9H).

Workup

  1. customthe solvent removed

Sources & evidence

ORD record
ord-0fefa28603874c558d0fe8359ca83a30
Source dataset
uspto-grants-2007_03
Patent number
US07189720B2

Reaction notes

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