Ammonia → [5-Methoxy-2-(6-methoxybenzothiazol-2-yl)phenyl][4-(2-piperidin-1-ylethoxy)benzyl]amine

HRID 1950275Notes

Reaction equation

HRID 1950275 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[C:7]([NH2:9])[CH:8]=1.[N:21]1([CH2:27][CH2:28][O:29][C:30]2[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.N>O1CCCC1.ClCCl.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[C:7]([NH:9][CH2:34][C:33]2[CH:32]=[CH:31][C:30]([O:29][CH2:28][CH2:27][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:37][CH:36]=2)[CH:8]=1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 111838924-(2-(Piperidin-1-yl)ethoxy)benzaldehydeHCID 230875225-Methoxy-2-(6-methoxybenzothiazol-2-yl)phenylamine

Product 1

HCID 57933790[5-Methoxy-2-(6-methoxybenzothiazol-2-yl)phenyl][4-(2-piperidin-1-ylethoxy)benzyl]amineYield 15.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-methoxy-2-(6-methoxybenzothiazol-2-yl)phenylamine (473 mg) and 4-(2-piperidin-1-ylethoxy)benzaldehyde (484 mg) in tetrahydrofuran (6 ml), dichloromethane (4 ml) and acetic acid (4 ml) was added borane-methyl sulfide complex (0.18 ml), and the solution was stirred for 6 hours at room temperature. The solution was neutralized with ammonia solution on an ice bath, extracted with ethyl acetate, then sequentially washed with water and brine, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (132 mg).

Workup

  1. additionwas added borane-methyl sulfide complex (0.18 ml)
  2. extractionextracted with ethyl acetate
  3. washsequentially washed with water and brine
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-5018dcfbc7d446afbd488243532fd30a
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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