Water → HCID 23504858, compound

HRID 324367Notes

Reaction equation

HRID 324367 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:11][N:12]2[CH2:17][CH2:16][C:15]([OH:29])([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C(N([CH2:35][CH3:36])CC)C.Cl[CH2:38][C:39](Cl)=[O:40].[OH2:42]>ClCCl>[C:39]([NH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:11][N:12]2[CH2:17][CH2:16][C:15]([O:29][C:35](=[O:42])[CH3:36])([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1)(=[O:40])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 23504853HCID 23504853, compound

Product 1

HCID 23504858HCID 23504858, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(6-aminoindan-1-ylmethyl)-4-hydroxy-4-(3-trifluoromethyl-4-chlorophenyl)piperidine, 2j, (6.7 g) and triethylamine (4 mL) in dichloromethane (100 mL) was added dropwise at 0-5° C. a solution of chloroacetylchloride (2.6 mL) in dichloromethane (50 mL). The mixture was stirred overnight at room temperature. Water was added and pH was adjusted to >9. The organic phase was separated and worked up as previously. The crude product was purified by column chromatography on silica gel (eluted with 4% triethylamine in ethyl acetate). Yield of pure 18a 6.2 g as an oil.

Workup

  1. customThe organic phase was separated
  2. customThe crude product was purified by column chromatography on silica gel (eluted with 4% triethylamine in ethyl acetate)

Sources & evidence

ORD record
ord-17d267085aa9437bacc86e3ae2e87a66
Source dataset
uspto-grants-2001_04
Patent number
US06218394B1

Reaction notes

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