1,2-Diaminocyclohexane → HCID 59301831, compound

HRID 1819983Notes

Reaction equation

HRID 1819983 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.N[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[NH2:19].[C:20]([BH3-])#[N:21].[Na+]>CO>[CH2:10]1[O:11][C:3]2[CH:2]=[CH:1][C:6]([CH2:7][NH:19][C@@H:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C@H:13]3[NH:21][CH2:20][C:1]3[CH:6]=[CH:5][C:4]4[O:9][CH2:10][O:11][C:3]=4[CH:2]=3)=[CH:5][C:4]=2[O:9]1

Participants

5

Reactant 3

HCID 46101,2-DiaminocyclohexaneHCID 8438PiperonalHCID 5003444Sodium cyanoborohydride

Product 1

HCID 59301831HCID 59301831, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of piperonal (0.8 g, 5.3 mmol) and 1,2-diaminocyclohexane (0.296 g, 2.6 mmol) in dry methanol (25 ml) was added sodium cyanoborohydride (0.38 g, 6 mmol) and the mixture stirred for 48 h. The mixture was filtered and the solvents removed in vacuo to give the crude product. Crystallization from methanol gave DC-0012B as an off-white crystalline solid (0.298 g, 30%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvents removed in vacuo
  3. customto give the crude product
  4. customCrystallization from methanol

Sources & evidence

ORD record
ord-41ed337270524f0c92aa350ad26f3f2b
Source dataset
uspto-grants-2009_10
Patent number
US07601876B2

Reaction notes

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