Nitrogen → 3-Hydroxymethyl-4-[(1,2,3,4-tetrahydro-naphthalen-1-ylamino)-methyl]-benzonitrile

HRID 251281Notes

Reaction equation

HRID 251281 reaction equation
[C:1]([C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]([CH:21]2[C:30]3N=[CH:28][CH:27]=[CH:26][C:25]=3[CH2:24][CH2:23][CH2:22]2)S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)=[C:5]([CH2:33][OH:34])[CH:4]=1)#[N:2].[C:35]([O-])([O-])=O.[K+].[K+].C1(S)C=CC=CC=1.N#N>CN(C=O)C>[OH:34][CH2:33][C:5]1[CH:4]=[C:3]([CH:32]=[CH:31][C:6]=1[CH2:7][NH:8][CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:35]=2)[CH2:24][CH2:23][CH2:22]1)[C:1]#[N:2]

Participants

6

Reactant 4

HCID 947NitrogenHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 67272149N-(4-cyano-2-hydroxymethyl-benzyl)-2-nitro-N-(5,6,7,8-tetrahydro-quinolin-8-yl)-benzenesulfonamide

Product 1

HCID 672729943-Hydroxymethyl-4-[(1,2,3,4-tetrahydro-naphthalen-1-ylamino)-methyl]-benzonitrileYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-cyano-2-hydroxymethyl-benzyl)-2-nitro-N-(5,6,7,8-tetrahydro-quinolin-8-yl)-benzenesulfonamide (2.32 g, 4.85 mmol) dissolved in DMF (50 mL) was added K2CO3 (3.35 g, 24.3 mmol) and thiophenol (1.49 mL, 14.6 mmol). The solution was stirred at room temperature under a positive pressure of N2 for 3 hours. The mixture was concentrated in vacuo and redissolved in CH2Cl2 (50 mL). The mixture was filtered through a sintered glass funnel containing celite. The solution was concentrated in vacuo to afford a yellow solid. Purification via column chromatography on silica gel (hexane:EtOAc, 1:1, v/v) afforded 3-hydroxymethyl-4-[(1,2,3,4-tetrahydro-naphthalen-1-ylamino)-methyl]-benzonitrile as a yellow solid (1.22 g, 86%). 1H NMR (CDCl3) δ 1.92 (m, 3H), 2.26 (m, 1H), 2.77 (m, 2H), 3.86 (m, 1H), 4.02 (d, 1H, J=13.3 Hz), 4.17 (d, 1H, J=12.3 Hz), 4.51 (d, 1H. J=12.3 Hz), 4.80 (d, 1H, J=11.4 Hz), 7.09 (dd, 1H, J=8.3, 5.3 Hz), 7.42 (d, 1H, J=6.6 Hz), 7.49 (d, 1H, J=7.9 Hz), 7.59 (m, 1H), 7.64 (s, 1H), 8.35 (d, 1H, J=4.8 Hz).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionredissolved in CH2Cl2 (50 mL)
  3. filtrationThe mixture was filtered through a sintered glass funnel
  4. additioncontaining celite
  5. concentrationThe solution was concentrated in vacuo
  6. customto afford a yellow solid
  7. customPurification via column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-e04117fdc49344f2b739eaa5cebde402
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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