Water → HCID 70046208, compound

HRID 1419933Notes

Reaction equation

HRID 1419933 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O[CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][C:36]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=2)([OH:39])[CH2:35][CH2:34]1.O>CN(C=O)C.C(Cl)Cl>[OH:39][C:36]1([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=2)[CH2:37][CH2:38][N:33]([CH2:32][CH2:31][O:14][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:17][CH:16]=2)[CH2:34][CH2:35]1

Participants

7

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 738804-(Benzyloxy)benzoic acidHCID 54242644HCID 54242644, compound

Product 1

HCID 70046208HCID 70046208, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

4-Benzyloxybenzoic acid (0.685 g, 3 mmol) was dissolved in DMF (6 ml), and 1,1,-carbonyldiimidazole (0.58 g, 3.6 mmol) was added portionwise. The reaction mixture was heated to 55°-60° C. for 20 min. and then cooled to room temperature. A solution of 1-(2-hydroxy-ethyl)-4-(4-methyl-benzyl)-piperidin-4-ol (0.78 g, 3.3 mmol) in DMF (2 ml) was added. The reaction mixture was stirred 23 hours at room temperature and 4 hours at 60° C. H2O (50 ml) was added followed by CH2Cl2. Organic phase was washed with sat. NaHCO3, dried over Na2SO4, and concentrated. The residue was chromatographed over silica gel (CH2Cl2 --MeOH, 19:1) to provide 4-benzyloxy-benzoic acid 2-[4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-yl]-ethyl ester (0.65 g, 47%) as a colorless solid, m.p. 102° C. and MS: m/e=460.3 (M+H+).

Workup

  1. temperatureThe reaction mixture was heated to 55°-60° C. for 20 min.
  2. washOrganic phase was washed with sat. NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel (CH2Cl2 --MeOH, 19:1)

Sources & evidence

ORD record
ord-c9fe4c994ace4ea7a47d9c4696a7bfca
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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