Benzoyl chloride → HCID 53884909, compound

HRID 1086261Notes

Reaction equation

HRID 1086261 reaction equation
[C:1]1([CH2:7][O:8][CH:9]2[CH:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:12]([CH2:31][O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:11]([CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:10]2[CH:47]([CH2:49][CH:50]=[CH2:51])[OH:48])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:59](Cl)(=[O:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[C:59]([O:48][CH:47]([CH2:49][CH:50]=[CH2:51])[CH:10]1[CH:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:12]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:11]1[CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)(=[O:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 53675289HCID 53675289, compound

Product 1

HCID 53884909HCID 53884909, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound (XIII) (3.00 g; 4.40 mmoles) and triethyl amine (2.4 mL; 17.6 mmoles) in methylene chloride (25 mL), cooled at 0° C., was added benzoyl chloride (1.6 mL; 13.2 mmoles). The reaction was kept at room temperature for 16 hours, then water (5 mL) and saturated aqueous sodium bicarbonate solution (40 mL) were added. The phases were separated, and the aqueous phase was extracted with methylene chloride (30 mL). The combined organic solution was dried over sodium sulfate and the solvent evaporated under reduced pressure. The crude oil was purified via flash chromatography (silica gel; 1:4 ethyl acetate:hexane) to yield 3,4,5-tris(phenylmethoxy)-6-[(phenylmethoxy) methyl]-1-(phenylmethyl)-α-(2-propenyl)-2-piperidinemethanol benzoate (ester) (XIV) (1.92 g; 56%) as a clear, colorless oil and recovered Compound (XIII) (0.60 g; 0.88 mmoles). IR (neat) 1719 cm-1 (C=0); MS (FAB-MNBA) 788 (MH+), 680 (MH + --PhCH2OH); 1H nmr (CDCl3) δ 2.4 (m, 1H), 2.9 (dt, 1H), 3.5-4.0 (m, 8H), 4.1 (d, 1H), 4.4 (s, 2H), 4.5-4.9 (m, 9H), 5.4-5.6 (m, 1H), 7.1-7.4 (m, 27H), 7.5 (m, 1H), 8.1 (m, 2H).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with methylene chloride (30 mL)
  3. dry with materialThe combined organic solution was dried over sodium sulfate
  4. customthe solvent evaporated under reduced pressure
  5. customThe crude oil was purified via flash chromatography (silica gel; 1:4 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-858f78e2fc5e4461948348e20fece074
Source dataset
uspto-grants-1991_07
Patent number
US05028614

Reaction notes

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