1,2-Diaminocyclohexane, trans- → trans-N,N'-Bis(2-diphenylphosphanylbenzylidene)cyclohexane-1,2-diamine

HRID 857830Notes

Reaction equation

HRID 857830 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH2:8].[C:9]1([P:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[CH:18]=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[C:9]1([P:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[CH:18]=[N:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]2[N:8]=[CH:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[P:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 438061,2-Diaminocyclohexane, trans-HCID 27543162-Diphenylphosphinobenzaldehyde

Product 1

HCID 11285891trans-N,N'-Bis(2-diphenylphosphanylbenzylidene)cyclohexane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.5 g of granulated molecular sieves (4A) are baked in a Schlenk tube. After addition of 50 ml of dichloromethane, 1.75 g (15 mmol) of trans-1,2-diaminocyclohexane and 8.7 g (30 mmol) of o-diphenylphosphinobenzaldehyde, the reaction mixture is stirred for 24 hours. After filtration through Celite, the solvent is removed and the residue is recrystallized with 50 ml of ethanol, giving the product in the form of a light-yellow powder in a yield of 8.6 g (13 mmol, 87%). 1H-NMR (400 MHz, CDCl3): δ=8.71 (d, J=4 Hz, 2H, N═C—H), 7.78–6.64 (m, 28 H, aromat. H), 3.16 (m, 2H, C—H), 1.66–1.31 (m, 8H, (CH2)4) ppm.

Workup

  1. filtrationAfter filtration through Celite
  2. customthe solvent is removed
  3. customthe residue is recrystallized with 50 ml of ethanol
  4. customgiving the product in the form of a light-yellow powder in a yield of 8.6 g (13 mmol, 87%)

Sources & evidence

ORD record
ord-3c6a34adb04a4030b60ccec8baca4085
Source dataset
uspto-grants-2006_12
Patent number
US07148174B2

Reaction notes

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