Hydrochloric Acid → HCID 23326053, compound

HRID 1980136Notes

Reaction equation

HRID 1980136 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)([C:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][CH:15]=2)O)=[CH:4][CH:3]=1.[ClH:30].[O:31]1CCCC1>>[ClH:30].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[C:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][CH:15]2[OH:31])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 23326057HCID 23326057, compound

Product 1

HCID 23326053HCID 23326053, compoundYield 58.7%

Conditions

Temperature
10 °C

Procedure

To a stirred solution of 50.9 parts of α,α-bis(4-fluorophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinemethanol in 270 parts of tetrahydrofuran were added 750 parts of a hydrochloric acid solution 1N. The whole was stirred first for 7 hours at reflux temperature and then for 8 hours at room temperature. The precipitated product was filtered off and set aside. The filtrate was evaporated till all traces of tetrahydrofuran were removed. After cooling, the solid precipitated product was filtered off and suspended, together with the precipitated product which was set aside (see above), in 80 parts of acetonitrile. The product was filtered off and stirred in 40 parts of acetonitrile while heating. After cooling to 10° C., the product was filtered off and dried, yielding 32.6 parts (58.7%) of 4-[bis(4-fluorophenyl)-methylene]-1-(phenylmethyl)-3-piperidinol hydrochloride; mp. 266° C. (intermediate 23).

Workup

  1. temperatureat reflux temperature
  2. waitfor 8 hours at room temperature
  3. filtrationThe precipitated product was filtered off
  4. customThe filtrate was evaporated till all traces of tetrahydrofuran
  5. customwere removed
  6. temperatureAfter cooling
  7. customthe solid precipitated product
  8. filtrationwas filtered off
  9. filtrationThe product was filtered off
  10. stirringstirred in 40 parts of acetonitrile
  11. temperaturewhile heating
  12. filtrationthe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-2665db47842849e5a2f4c9c13c7f14cd
Source dataset
uspto-grants-1984_11
Patent number
US04485107

Reaction notes

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