Ammonium Chloride → HCID 20277028, compound

HRID 1248618Notes

Reaction equation

HRID 1248618 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH:5]2[CH:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([Mg]Br)=[CH:22][CH:21]=1.[NH4+].[Cl-]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8]([C:7]([C:23]3[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=3)([OH:11])[CH2:6][CH:5]2[CH:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 20277034HCID 20277034, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 20277028HCID 20277028, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Fluoro-3-(1-methyl-4-piperidyl)indanone (100 g) (prepared according to standard methods--J. Med. Chem., 11, (1968), 1064-66) in dry tetrahydrofuran (500 ml) was added dropwise to 4-fluorophenylmagnesium bromide (from 95 g of 4-bromofluorobenzene and 20 g of Mg-turnings in 500 ml of dry tetrahydrofuran). The reaction mixture was poured into NH4Cl (100 g) and crushed ice (3 L) and extracted with ether (2×300 ml). The combined organic phases were extracted with 0.5M CH3COOH (2×500 ml). The acid H2O-phase was made alkaline with 2M NaOH solution and extracted with ether (2×200 ml). The combined ether-phases were worked up as above and the starting material removed by washing with light petroleum. The title compound crystallized from isopropylether. Yield: 16.5 g (11.7%). MP: 148°-150° C.

Workup

  1. extractionextracted with ether (2×300 ml)
  2. extractionThe combined organic phases were extracted with 0.5M CH3COOH (2×500 ml)
  3. extractionextracted with ether (2×200 ml)
  4. customremoved
  5. washby washing with light petroleum
  6. customThe title compound crystallized from isopropylether

Sources & evidence

ORD record
ord-2aea706d0eb4432e9650d24e53a13e08
Source dataset
uspto-grants-1985_06
Patent number
US04525360

Reaction notes

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