Hydrochloric Acid → HCID 53735636, compound

HRID 1266189Notes

Reaction equation

HRID 1266189 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH:15]([C:17]3[CH:26]=[CH:25][C:20]4[NH:21][C:22](=[O:24])[O:23][C:19]=4[CH:18]=3)O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+].O>O1CCOCC1.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH:14]=[CH:15][C:17]3[CH:26]=[CH:25][C:20]4[NH:21][C:22](=[O:24])[O:23][C:19]=4[CH:18]=3)[CH2:9][CH2:8]2)=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 10200036HCID 10200036, compound

Product 1

HCID 53735636HCID 53735636, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 6.7 g of 6-{3-[4-(4-fluorobenzyl)piperid-1-yl]-1-hydroxypropyl}-3H-benzoxazol-2-one [obtainable by hydrogenation of 6-{3-[4-(4-fluorobenzyl)piperid-1-yl]-1-oxopropyl}-3H-benzoxazol-2-one, which can be obtained by reacting 4-(4-fluorobenzyl)piperidine and 6-(3-chloropropionyl)-3H-benzoxazol-2-one] in 70 ml of dioxane is heated under reflux with 7 ml of concentrated HCl for 1.5 h. The mixture is cooled and 8.5 g of NaHCO3 and 70 ml of water are added. 30 ml of dichloromethane are added and the mixture is stirred for 30 minutes. The precipitate is separated off, washed with acetone and ether and dried to give 5.7 g of 6-{3-[4-(4-fluorobenzyl)piperid-1-yl]propenyl}-3H-benzoxazol-2-one (“A”), m.p. 202-203.5°; hydrochloride: m.p. 220-223°.

Workup

  1. temperatureThe mixture is cooled
  2. customThe precipitate is separated off
  3. washwashed with acetone and ether
  4. customdried

Sources & evidence

ORD record
ord-547346e156a54a01b9d1ed34506235f4
Source dataset
uspto-grants-2003_04
Patent number
US06548516B1

Reaction notes

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