Water → N1,N2-bis(2-(diphenylphosphino)benzyl)cyclohexane-1,2-diamine

HRID 1895833노트

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HRID 1895833 반응식
[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

참가 물질

5

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 5242762HCID 5242762, 화합물

생성물 1

HCID 12075083N1,N2-bis(2-(diphenylphosphino)benzyl)cyclohexane-1,2-diamine

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9518cc6139a3497694b19109ad9667ce
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518368B2

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