Diethyl Ether → HCID 10369286, compound

HRID 346805Notes

Reaction equation

HRID 346805 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11](=[O:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[NH:19][CH:18]=2)[CH2:5][CH2:4]1.Cl[Si](C)(C)C.CCOCC>CC(=O)CC>[ClH:26].[CH3:34][N:2]([CH3:1])[C:3]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:4][CH2:5][CH:6]([CH2:9][NH:10][C:11](=[O:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[NH:19][CH:18]=2)[CH2:7][CH2:8]1.[CH3:34][N:2]([CH3:1])[C:3]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:4][CH2:5][CH:6]([CH2:9][NH:10][C:11](=[O:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[NH:19][CH:18]=2)[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 10369287HCID 10369287, compound

Product 2

HCID 10369286HCID 10369286, compoundHCID 10369287HCID 10369287, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In the manner described for Example 23, 97 mg (0.20 mmol.) of the polar diastereoisomer of 6-(5-chloro-1H-indol-3-yl)hexanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide were also obtained and were dissolved in 2-butanone (5 ml); chlorotrimethylsilane (38 μl, 0.30 mmol.) was added thereto. There immediately formed a white precipitate, which was deposited in a tacky manner on the wall of the flask. The solvent was reduced to about 0.5 ml in vacuo, ether (2 ml) was added to the residue, and vigorous stirring was carried out for 1 h. The solid that formed was filtered off with suction, washed with ether (2×1 ml) and dried in vacuo. The hydrochloride of the polar diastereoisomer of 6-(5-chloro-1H-indol-3-yl)hexanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide was thus obtained in the form of a slightly hygroscopic solid in a yield of 109 mg (m.p. 110–125° C.).

Workup

  1. customwere also obtained
  2. customThere immediately formed a white precipitate, which
  3. additionwas added to the residue
  4. customThe solid that formed
  5. filtrationwas filtered off with suction
  6. washwashed with ether (2×1 ml)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a56e58f77d7140f2ac62847a6b403352
Source dataset
uspto-grants-2007_02
Patent number
US07173045B2

Reaction notes

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