[2-(1-Ethyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-5-methyl-phenyl]-carbamic acid tert-butyl ester → 2-(1-Ethyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-5-methyl-phenylamine

HRID 1821769Notes

Reaction equation

HRID 1821769 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[O:15][CH2:16][CH:17]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([CH2:27][CH3:28])[CH2:18]1)(C)(C)C>Cl.O1CCOCC1>[CH2:27]([N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:26][CH:17]([CH2:16][O:15][C:9]2[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=2[NH2:7])[CH2:18]1)[CH3:28]

Participants

4

Reactant 1

HCID 67254063[2-(1-Ethyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-5-methyl-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 220463702-(1-Ethyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-5-methyl-phenylamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of [2-(1-Ethyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-5-methyl-phenyl]-carbamic acid tert-butyl ester (40 mg, 0.1 mmol) was stirred in 4N HCl in dioxane (2 mL) at room temperature under a drying tube overnight. The suspension was concentrated by rotovap, diluted to 30 mL with CH2Cl2 and shaken with 10% Na2CO3 (30 mL). The organics were isolated, dried (MgSO4), filtered and concentrated to a brown oil, which was used without purification in the following reaction.

Workup

  1. concentrationThe suspension was concentrated by rotovap
  2. additiondiluted to 30 mL with CH2Cl2
  3. customThe organics were isolated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a brown oil, which
  7. customwas used without purification in the following reaction

Sources & evidence

ORD record
ord-fd11d51bfce146fdbf08397abea0cd06
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

Loading…