Triethylamine → 3-(2-Hydroxyethyl)-3-(3,4-dichlorophenyl)-1-[(3-isopropoxyphenyl)acetyl]piperidine

HRID 742633Notes

Reaction equation

HRID 742633 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][CH2:10][C:11]1([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]1.[CH:25]([O:28][C:29]1[CH:30]=[C:31]([CH2:35][C:36](O)=[O:37])[CH:32]=[CH:33][CH:34]=1)([CH3:27])[CH3:26].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[OH:8][CH2:9][CH2:10][C:11]1([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:16][CH2:15][CH2:14][N:13]([C:36](=[O:37])[CH2:35][C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([O:28][CH:25]([CH3:26])[CH3:27])[CH:30]=2)[CH2:12]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 154604002-[3-(3,4-Dichlorophenyl)piperidin-3-yl]ethanolHCID 166389242-(3-(Propan-2-yloxy)phenyl)acetic acid

Product 1

HCID 183333523-(2-Hydroxyethyl)-3-(3,4-dichlorophenyl)-1-[(3-isopropoxyphenyl)acetyl]piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

22.5 ml of triethylamine and then 22 g of the 3-(2-hydroxyethyl)-3-(3,4-dichlorophenyl)piperidine (-) prepared above according to PREPARATION III (f) are added to a solution of 16 g of 3-isopropoxyphenylacetic acid in 500 ml of CH2Cl2. The mixture is cooled to 0° C., 42.6 g of BOP are then added and the reaction mixture is allowed to warm up to room temperature. After 30 minutes, the mixture is concentrated under vacuum and the residue is taken up in ether and washed successively with water, a dilute solution of NaOH, a saturated solution of NaCl, a dilute solution of HCl, a saturated solution of NaCl and a solution of NaHCO3. The ether phase is dried over MgSO4, filtered and concentrated under vacuum to give 36 g of optically pure product.

Workup

  1. temperatureto warm up to room temperature
  2. concentrationthe mixture is concentrated under vacuum
  3. washwashed successively with water
  4. dry with materialThe ether phase is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give 36 g of optically pure product

Sources & evidence

ORD record
ord-615f85f0996a45168dbb76164f2308a9
Source dataset
uspto-grants-1996_09
Patent number
US05554763

Reaction notes

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