Benzyl Bromide → N-benzyl-N-[[4-[(2-pyridylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine

HRID 351177Notes

Reaction equation

HRID 351177 reaction equation
[N+](C1C=CC=CC=1S([N:13]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22][CH:23]2[C:32]3[N:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:26][CH2:25][CH2:24]2)=[CH:17][CH:16]=1)(=O)=O)([O-])=O.C([O-])([O-])=O.[K+].[K+].[CH2:46](Br)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CC#N>[N:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:23]2[C:32]3[N:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:26][CH2:25][CH2:24]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22018658N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Product 1

HCID 22256447N-benzyl-N-[[4-[(2-pyridylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amineYield 60.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.220 g, 0.390 mmol) in CH3CN (8 mL), at room temperature, was added powdered K2CO3 (0.153 g, 1.11 mmol) followed by excess benzyl bromide (0.20 mL, 1.68 mmol). After 18 hours, the reaction mixture was concentrated and the residue was partitioned between CH2Cl2 (10 mL) and water (5 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography (2 mm plate, 20:1 CH2Cl2—CH3OH) provided the desired product (0.106 g, 44%) as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was partitioned between CH2Cl2 (10 mL) and water (5 mL)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (2×10 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification of the crude material by radial chromatography (2 mm plate, 20:1 CH2Cl2—CH3OH)

Sources & evidence

ORD record
ord-5096eb010d7c49cdaccdb9cc1ff791e4
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

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