Water → Methyl 4-({{4-[(4-butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)-ethyl]amino}methyl)benzoate

HRID 551895Notes

Reaction equation

HRID 551895 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:29]=[CH:28][C:16]([CH2:17][NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH:30]([C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:29]=[CH:28][C:16]([CH2:17][N:18]([CH2:30][C:32]3[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=3)[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 15294Methyl 4-FormylbenzoateHCID 5049666Sodium triacetoxyborohydrideHCID 57554507{4-[(4-Butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)ethyl]amine

Product 1

HCID 11519626Methyl 4-({{4-[(4-butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)-ethyl]amino}methyl)benzoateYield 73%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of {4-[(4-butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)ethyl]amine (2.85 g, 7.1 mmol) and methyl 4-formylbenzoate (1.16 g, 7.1 mmol) in DCE (24 mL) was added at once sodium triacetoxyborohydride (2.25 g, 10.6 mmol) and the resulting reaction mixture was stirred 12 hrs at rt. The reaction mixture was poured into water and extracted with DCM. The combined organic layers were dried over MgSO4 and the solvents were removed under reduced pressure to give the crude product. Purification by chromatography on silicagel (EtOAc/c-hex (5/95)) gave 2.8 g (73%) of the title compound as a white solid. HPLC, Rt: 5.0 min (purity: 99.9%). 1H NMR (CDCl3) δ: 7.98 (d, J=8.3 Hz, 2H), 7.51-7.43. (m, 4H), 7.36 (d, J=8.3 Hz, 2H), 7.29-7.15 (m, 6H), 7.00 (d, J=8.3 Hz, 2H), 3.94 (s, 3H), 3.68 (s, 2H), 3.64 (s, 2H), 2.83-2.59 (m, 6H), 1.69-1.55 (m, 2H), 1.44-1.30 (m, 2H), 0.95 (J=7.2 Hz, 3H).

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customto give the crude product
  6. customPurification by chromatography on silicagel (EtOAc/c-hex (5/95))

Sources & evidence

ORD record
ord-7a9d493e7d37480db7de8329327e56b8
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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