Sodium Carbonate → HCID 21402974, compound

HRID 1287629Notes

Reaction equation

HRID 1287629 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH2:16][NH2:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1.ClC[CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24].C(=O)([O-])[O-:27].[Na+].[Na+]>C1C=CC=CC=1.O>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH2:16][NH:17][C:20](=[O:27])[CH2:21][CH2:22][CH2:23][OH:24])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 740895-Chlorovaleryl chlorideHCID 2020415H-Dibenzo(a,d)cycloheptene-5-methylamine, 10,11-dihydro-

Product 1

HCID 21402974HCID 21402974, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-methylamine (20.0 g), 5-chlorovaleric acid chloride (19.2 g) and sodium carbonate (35.0 g) in 250 ml of benzene is stirred and subjected to reflux for 16 hours. The reaction mixture is diluted with water. The benzene layer is separated and washed with water, dried and evaporated to dryness The residue is crystallized from benzene-hexane to afford the haloamide N-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-5-chlorovaleramide (III, Alk = CH2CH2CH2CH2 and Y = Cl), m.p.., 98°-99° C.

Workup

  1. temperatureto reflux for 16 hours
  2. customThe benzene layer is separated
  3. washwashed with water
  4. customdried
  5. customevaporated to dryness The residue
  6. customis crystallized from benzene-hexane

Sources & evidence

ORD record
ord-f2815cefc5884ecdb7e67230fe7c9ba6
Source dataset
uspto-grants-1976_10
Patent number
US03985751

Reaction notes

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