Benzene → HCID 11247180, compound

HRID 900047Notes

Reaction equation

HRID 900047 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]=[CH:16][C:17]1[C:30]2[C:31]3=[C:32]4[C:27](=[CH:28][CH:29]=2)[CH:26]=[CH:25][CH:24]=[C:23]4[CH:22]=[CH:21][C:20]3=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C1C=CC=CC=1>CO>[CH2:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]1[C:30]2[C:31]3=[C:32]4[C:27](=[CH:28][CH:29]=2)[CH:26]=[CH:25][CH:24]=[C:23]4[CH:22]=[CH:21][C:20]3=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 4311764Sodium borohydrideHCID 13008363HCID 13008363, compound

Product 1

HCID 11247180HCID 11247180, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-benzyl-N′-pyren-1-ylmethylene-hexane-1,6-diamine (420 mg, 1.00 mmol) and sodium borohydride (190 mg, 5.00 mmol) in methanol (10.0 ml) was stirred at room temperature for 3 hours under a nitrogen atmosphere. The solvent was removed under vacuum, and the residue was dissolved in chloroform and washed with water, and dried over magnesium sulphate. The solvent was removed and the residue was dried under vacuum to give a yellow oil (386/mg, 92%). 1H NMR (CDCl3) δ/ppm 1.32 (4H, m, (CH2)2), 1.45 (2H, m, BnNCCH2), 1.55 (2H, m, PyCNCCH2), 2.55 (2H, t, BnNCH2), 2.75 (2H, t, PyCNCH2), 3.75 (2H, s, PhCH2), 4.50 (2H, s, PyCH2), 7.15-7.25 (5H, m, Ph-H), 7.95-8.10, 8.15-8.22, 8.37 (4H, 4H, 1H respectively, m, m, d, Py-H). 13C NMR (CDCl3) δ/ppm 27.35, 30.16, 49.46, 50.02, 51.94, 54.13, 54.13, 123.19, 124.72, 125.00, 125.09, 125.89, 126.89, 127.03, 127.50, 127.64, 128.14, 128.40, 129.06, 131.34, 134.15; m/z (EI) 420 ([M])+, 7%).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was removed
  6. customthe residue was dried under vacuum
  7. customto give a yellow oil (386/mg, 92%)

Sources & evidence

ORD record
ord-0a40f6c5b7914110b6920540b0533b27
Source dataset
uspto-grants-2008_04
Patent number
US07358094B2

Reaction notes

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