Triethylamine → HCID 57072383, compound

HRID 1493400Notes

Reaction equation

HRID 1493400 reaction equation
Cl[P:2]1[O:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][O:3]1.[CH2:10]([NH:22][CH:23]1[CH2:28][C:27]([CH3:30])([CH3:29])[N:26]([O:31][CH:32]([CH3:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:25]([CH3:41])([CH3:40])[CH2:24]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(N(CC)CC)C.Cl.C(N(CC)CC)C>O1CCCC1>[CH3:8][C:5]1([CH3:9])[CH2:6][O:7][P:2]([N:22]([CH:23]2[CH2:28][C:27]([CH3:29])([CH3:30])[N:26]([O:31][CH:32]([CH3:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:25]([CH3:40])([CH3:41])[CH2:24]2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[O:3][CH2:4]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 755081,3,2-Dioxaphosphorinane, 2-chloro-5,5-dimethyl-HCID 19768353HCID 19768353, compound

Product 1

HCID 57072383HCID 57072383, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.03 grams (18.0 mmol) of 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane in 10 ml of tetrahydrofuran is added over ten minutes to a solution of 8.00 grams (18.0 mmol ) of 4-dodecylamino-1-alpha-methylbenzyloxy2,2,6,6-tetramethylpiperidine, 1.91 grams (18.9 mmol) of triethylamine, and 25 ml of tetrahydrofuran. The reaction temperature increases from 20° C. to 30° C. during the addition, and triethylamine hydrochloride precipitates from solution. The reaction mixture is stirred at ambient temperature for two hours. The precipitate is removed by filtration, and the filtrate is concentrated at reduced pressure. Residual volatiles are removed by Kugelrohr distillation (at 100° C./0.2 mm) to afford 10.1 grams (97% yield) of the title compound as a viscous oil.

Workup

  1. customprecipitates from solution
  2. customThe precipitate is removed by filtration
  3. concentrationthe filtrate is concentrated at reduced pressure
  4. customResidual volatiles are removed by Kugelrohr distillation (at 100° C./0.2 mm)

Sources & evidence

ORD record
ord-271e4c914c294ae1bee6076a53e8eaad
Source dataset
uspto-grants-1991_06
Patent number
US05021481

Reaction notes

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