Water → N1,N2-Bis[[2-(diphenylphosphino)phenyl]methyl]-1,2-cyclohexanediamine

HRID 1895833Notes

Reaction equation

HRID 1895833 reaction equation
[C:1]1([P:7]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:8]2[CH:42]=[CH:41][CH:40]=[CH:39][C:9]=2[CH:10]=[N:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[N:18]=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O>C(O)C>[C:33]1([P:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH2:19][NH:18][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]2[NH:11][CH2:10][C:9]2[CH:39]=[CH:40][CH:41]=[CH:42][C:8]=2[P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 5242762HCID 5242762, compound

Product 1

HCID 12075083N1,N2-Bis[[2-(diphenylphosphino)phenyl]methyl]-1,2-cyclohexanediamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N1,N2-bis(2-(diphenylphosphino)benzylidene)cyclohexane-1,2-diamine (2.18 g, 2.83 mmol) (prepared according to the literature procedure: Laue, S.; Greiner, L.; Woltinger, J.; Liese, A. Adv. Synth. Catal. 2001, 343, 711) and sodium borohydride (NaBH4) (0.64 g, 17 mmol) in ethanol (30 ml) was refluxed with stirring for 6 hours. The resulting solution was cooled to room temperature and water (15 ml) was added to destroy excess NaBH4. The mixture was extracted with dichloromethane and the combined extracts were washed with saturated aqueous ammonium chloride solution [NH4Cl] and then water. The organic layer was dried over magnesium sulfate and then filtered through silica gel. The filtrate was then evaporated to dryness to obtain a yellow solid. Yield: 2.0 g (91%). 1H NMR (400 MHz, CD2Cl2): δ 7.58-6.80 (m, 20H, Ph-H), 3.86 (d, 4H, NCH2), 3.65 (br, 2H, NH), 2.21 (s, 24H, CH3), 1.80 (m, 8H, cyclohexane-H). 31P{1H} NMR (162 MHz, CD2Cl2): δ−13.

Workup

  1. customprepared
  2. customto destroy excess NaBH4
  3. extractionThe mixture was extracted with dichloromethane
  4. washthe combined extracts were washed with saturated aqueous ammonium chloride solution [NH4Cl]
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered through silica gel
  7. customThe filtrate was then evaporated to dryness
  8. customto obtain a yellow solid

Sources & evidence

ORD record
ord-9518cc6139a3497694b19109ad9667ce
Source dataset
uspto-grants-2013_08
Patent number
US08518368B2

Reaction notes

Loading…