Toluene → HCID 19764421, compound

HRID 247831Notes

Reaction equation

HRID 247831 reaction equation
C1([N:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[P:8](=[O:11])([OH:10])[OH:9])C=CC=CC=1.C(N)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.[C:36]1([CH3:42])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:42]([N:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[P:8](=[O:9])([OH:10])[O:11][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 7504BenzylamineHCID 8471TriethylamineHCID 19764441HCID 19764441, compound

Product 1

HCID 19764421HCID 19764421, compound

Procedure

To a solution of (±) phenyl nonyl phosphoryl chloride (Example C) (2.0 g, 6.3 mmol) in toluene (20 mL) at 0° C. is added a solution of benzylamine (0.67 g, 6.3 mmol) and triethylamine (1.3 mL, 9.4 mmol) in toluene (5 mL) over 5 minutes. The mixture is allowed to warm to room temperature and is stirred for 90 minutes. The mixture is filtered, and the filtrate concentrated. Flash chromatography (3:2 hexane/ethyl acetate) affords 2.1 g of the title compound as a colorless oil; 1H NMR (200 MHz, CDCl3)δ 7.40-7.10 (m, 10 H), 4.19 (dd, J=10 and 7 Hz, 2 H), 4.19-4.05 (m, 2 H), 3.20-3.00 (m, 1 H), 1.70-1.60 (m, 2 H), 1.35-1.20 (m, 12 H), 0.89 (t, J=7 Hz, 3 H).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-469bc2af1b7b4712b643037db1822bb4
Source dataset
uspto-grants-1993_05
Patent number
US05208224

Reaction notes

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