Hydrochloric Acid → HCID 20496734, compound

HRID 1074454Notes

Reaction equation

HRID 1074454 reaction equation
[Cl:1][CH2:2][CH:3](O)[CH2:4][CH2:5][O:6][C:7]1[CH:22]=[CH:21][C:10]2[CH2:11][CH:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:13][O:14][C:9]=2[CH:8]=1.[CH:24]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.Cl.C[OH:33]>>[ClH:1].[CH:24]1([NH:30][CH2:2][CH2:3][CH:4]([OH:33])[CH2:5][O:6][C:7]2[CH:22]=[CH:21][C:10]3[CH2:11][CH:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:13][O:14][C:9]=3[CH:8]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 7965CyclohexylamineHCID 20496746HCID 20496746, compound

Product 1

HCID 20496734HCID 20496734, compound

Procedure

A mixture of 6.64 g 1-chloro-4-(3-phenyl-3,4-dihydro-2H-1-benzopyrane-7-yloxy)-2-butanol and 3.7 cm3 cyclohexylamine was kept at 95° C. for 3 hours. The mixture was dissolved in 10 cm3 of methanol, 6 cm3 of methanol saturated with hydrochloric acid was added thereto, then the solution was evaporated. The residue was dissolved in 40 cm3 of benzene, the benzene solution was extracted with water and evaporated; 6.2 g crude 4-cyclohexylamino-1-(3-phenyl-3,4-dihydro-2H-1-benzopyrane-7-yloxy)-2-butanol-hydrochloride was obtained. The weight of the product crystallized from acetone is 5.0 g; melting point is 157°-159° C. The base liberated from its hydrochloric salt melts at 114°-116° C. The base can be transformed with methyl iodide into 1-(3-phenyl-3,4-dihydro-2H-1-benzopyrane-7-yloxy)-4-(dimethyl-cyclohexylammonium)-2-butanol-iodide (m.p. is 208°).

Workup

  1. customthe solution was evaporated
  2. dissolutionThe residue was dissolved in 40 cm3 of benzene
  3. extractionthe benzene solution was extracted with water
  4. customevaporated

Sources & evidence

ORD record
ord-49ec0d2e165049628d69109ef4e5b73e
Source dataset
uspto-grants-1983_07
Patent number
US04391821

Reaction notes

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