Hydrochloric Acid → 3-{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2'-(2-methoxyethyl)-3-methylbiphenyl-4-yl]propan-1-amine

HRID 2194887Notes

Reaction equation

HRID 2194887 reaction equation
[Cl:1][C:2]1[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([Cl:47])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH2:37][CH2:38][O:39][CH3:40])=[CH:27][C:26]=2[CH3:41])[CH2:16][NH:17]C(=O)OC(C)(C)C)=[CH:10][CH:9]=1.Cl.O1CCOCC1>C(Cl)Cl>[Cl:1][C:2]1[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([Cl:47])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH2:37][CH2:38][O:39][CH3:40])=[CH:27][C:26]=2[CH3:41])[CH2:16][NH2:17])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86658850Tert-butyl {3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2'-(2-methoxyethyl)-3-methylbiphenyl-4-yl]propyl}carbamate

Product 1

HCID 251916153-{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2'-(2-methoxyethyl)-3-methylbiphenyl-4-yl]propan-1-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2′-(2-methoxyethyl)-3-methylbiphenyl-4-yl]propyl}carbamate from step 4 (1 eq.) in CH2Cl2 (0.06M) at room temperature was added HCl 4M in dioxane (30 eq.). The reaction mixture was stirred for 3 h at room temperature and then concentrated to dryness. Purification by column chromatography on silica gel, eluting with CH2Cl2/MeOH(NH3 2M) 4%, afforded the title compound as a colorless oil. 1H NMR (400 MHz, acetone-d6): δ 7.46-7.20 (m, 6H); 7.22-7.12 (m, 2H); 7.07-6.97 (m, 3H); 6.81 (d, 2H); 4.39-4.32 (m, 4H); 3.60 (s, 3H); 3.55-3.45 (m, 2 H); 3.31-3.19 (m, 1H); 3.0-2.75 (m, 6H); 2.45 (t, 2H); 2.32 (s, 3H); 2.20 (s, 3H).

Workup

  1. concentrationconcentrated to dryness
  2. customPurification by column chromatography on silica gel
  3. washeluting with CH2Cl2/MeOH(NH3 2M) 4%

Sources & evidence

ORD record
ord-55f248916d66454698055553ec4652e1
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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