HCID 21921748, compound → HCID 131726858, compound

HRID 2221294Notes

Reaction equation

HRID 2221294 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH:13]([NH:15][CH3:16])[CH3:14])=[CH:8][CH:7]=[CH:6]2.[F:18][C:19]([F:36])([F:35])[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([Cl:34])=[O:33])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1>C(Cl)Cl>[ClH:34].[CH3:17][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH:13]([N:15]([CH3:16])[C:32]([C:29]1[CH:30]=[CH:31][C:26]([C:23]3[CH:24]=[CH:25][C:20]([C:19]([F:36])([F:35])[F:18])=[CH:21][CH:22]=3)=[CH:27][CH:28]=1)=[O:33])[CH3:14])=[CH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 21921748HCID 21921748, compoundHCID 69215882HCID 69215882, compound

Product 1

HCID 131726858HCID 131726858, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (6-dimethylamino-methyl-naphthalen-1-ylmethyl)-methyl-amine, 9, (14.25 g, 62.50 mmol), and 4′-trifluoromethyl-biphenyl-4-carbonyl chloride (17.81 g, 62.50 mmol) in CH2Cl2 (500 mL) is stirred at room temperature for 1 hr. The white solid which forms is collected by filtration and rinsed twice with CH2Cl2 (100 mL) to afford 22.0 g (69% yield) of the desired product as a white solid. 1H NMR (300 MHz, CD3OD): δ 8.37 (d, J=8.4 Hz, 1H), 8.15-7.56 (m, 13H), 5.31 (s, 2H), 5.31 and 5.14 (2×s, 2H, two rotamers), 3.17 and 2.93 (2×s, 9H, two rotamers). 13C NMR (75 MHz, CDCl3): δ 172.0, 165.5, 143.9, 141.4, 135.8, 134.1, 132.4, 132.1, 130.0, 129.0, 128.7, 127.7, 127.6, 127.4, 126.7, 126.6, 125.2, 123.9, 117.1, 61.1, 53.3, 42.1, 36.6. 19F NMR (282 MHz, CD3OD): δ 99.1. Mass Spec.: Calcd.: 477.5106; found HRMS: 477.5113; Formula: C29H27F3N2O+H, found LRMS: 477.27 (M+1).

Workup

  1. filtrationThe white solid which forms is collected by filtration
  2. washrinsed twice with CH2Cl2 (100 mL)

Sources & evidence

ORD record
ord-473b91ef05da4860bee629db6062335f
Source dataset
uspto-grants-2008_05
Patent number
US07368462B1

Reaction notes

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