1,2-Diaminocyclohexane → HCID 178483880, compound

HRID 706328Notes

Reaction equation

HRID 706328 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[CH2:15]([Li])CCC.CBr.C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:41](=[O:48])([O:43][C:44](C)(C)C)[NH2:42].S(Cl)(Cl)=O.Br[C:54]1[CH:59]=[CH:58][C:57]([NH2:60])=[C:56]([NH2:61])[CH:55]=1.NC1CCCCC1N>[Cu](I)I.C(O)=O>[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C@H:10]2[CH2:44][O:43][C:41](=[O:48])[N:42]2[C:54]2[CH:59]=[CH:58][C:57]3[NH:60][CH:15]=[N:61][C:56]=3[CH:55]=2)=[CH:8][CH:7]=1

Participants

10

Reactant 7

HCID 46101,2-DiaminocyclohexaneHCID 24386Thionyl ChlorideHCID 77922tert-Butyl carbamateHCID 84823p-(2-(Dimethylamino)ethoxy)benzaldehydeHCID 3235934-Bromobenzene-1,2-diamineHCID 21713226HCID 21713226, compoundHCID 178418339Butyllithium

Product 1

HCID 178483880HCID 178483880, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 284Formic AcidSolvent

Procedure

The compound was synthesized according to method 5 starting from 4-(2-(dimethylamino)ethoxy)benzaldehyde (3 g, 15.70 mmol), 2.3 M n-butyl lithium (13.65 mL, 15.7 mmol), triphenyl phosphonium methyl bromide (11.21 g, 17 mmol) T-butyl hypochlorite (2.7 mL, 22.32 mmol), t-butyl carbamate (2.66 g, 22.72 mmol) 0.4M aqueous sodium hydroxide (0.9 g in 57 mL water), osmate dihydrate (100 mg, 0.29 mmol), thionyl chloride (1.2 mL, 16.49 mmol), 4-bromo 1,2-diamino benzene (0.31 mg, 0.1.672 mmol), and copper iodide (44 mg, 0.228), 1,2-diaminocyclohexane (26 mg, 0.228), formic acid (3 mL). Yield: 0.110 g (2.0%); MS m/z 367.2 (M+H)+; 1H NMR (400 MHz, CDCl3): δ10.40 (Bs, 1H); 7.89 (s, 1H); 7.53 (s, 1H); 7.26-7.19 (merged with CDCl3, 5H); 6.81 (d, 2H); 5.33 (t, 1H); 4.79 (q, 1H); 4.25 (t, 1H); 4.00 (t, 2H); 2.70 (t, 2H); 2.34-2.25 (m, 6H); HPLC (λ=214 nm), [A]: rt 5.79 min (94.7%).

Workup

  1. customThe compound was synthesized
  2. customrt 5.79 min (94.7%)

Sources & evidence

ORD record
ord-e4c4658db17047ceaa7d050744da99a8
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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