Diethyl Ether → 4-(5-Fluoro-1H-indol-3-yl)butanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide hydrochloride

HRID 346803Notes

Reaction equation

HRID 346803 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11](=[O:25])[CH2:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)[CH2:5][CH2:4]1.[Cl:33][Si](C)(C)C.CCOCC>CC(=O)CC>[ClH:33].[CH3:32][N:2]([CH3:1])[C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11](=[O:25])[CH2:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)[CH2:5][CH2:4]1.[CH3:32][N:2]([CH3:1])[C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11](=[O:25])[CH2:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 102542024-(5-fluoro-1H-indol-3-yl)butanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide

Product 2

HCID 102542014-(5-Fluoro-1H-indol-3-yl)butanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide hydrochlorideHCID 102542024-(5-fluoro-1H-indol-3-yl)butanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In the manner described for Example 21, 240 mg (0.55 mmol.) of the polar diastereoisomer of 4-(5-fluoro-1H-indol-3-yl)butanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide were also obtained (m.p. 160–163° C.) and were dissolved in 2-butanone (7 ml); chlorotrimethylsilane (105 μl, 0.83 mmol.) was added thereto. There immediately formed a pale precipitate, which was deposited in a tacky manner on the wall of the flask. The solvent was reduced to about 3 ml in vacuo and, after addition of ether (3 ml), vigorous stirring was carried out for 1 h at RT. The solid that formed was filtered off with suction, washed with ether (3×1.5 ml) and dried in vacuo. The hydrochloride of the polar diastereoisomer of 4-(5-fluoro-1H-indol-3-yl)butanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide was thus obtained in the form of a hygroscopic solid in a yield of 234 mg.

Workup

  1. customwere also obtained (m.p. 160–163° C.)
  2. customThere immediately formed a pale precipitate, which
  3. customThe solid that formed
  4. filtrationwas filtered off with suction
  5. washwashed with ether (3×1.5 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e93d9e54a7a242afb69392810a666034
Source dataset
uspto-grants-2007_02
Patent number
US07173045B2

Reaction notes

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