Hydrochloric Acid → HCID 11811713, compound

HRID 1870247Notes

Reaction equation

HRID 1870247 reaction equation
C[O:2][C:3]([CH2:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17](=[O:30])[C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:20][C:19]=2[Cl:29])[CH2:9][CH2:8][CH2:7]1)=[O:4].[OH-].[Na+].Cl>CO>[C:3]([CH2:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17](=[O:30])[C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:20][C:19]=2[Cl:29])[CH2:9][CH2:8][CH2:7]1)([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 11102003Methyl 1-[2-chloro-4-(1-pyrrolidinyl)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine-5-acetate

Product 1

HCID 11811713HCID 11811713, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

5-Methoxycarbonylmethyl-1-[4-(1-pyrrolidinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (183 g) is suspended in methanol (2 liters), and thereto is added a 5N sodium hydroxide (171 ml), and the mixture is stirred at 60° C. for four hours. To the mixture is added a 5N sodium hydroxide (60 ml), and the mixture is stirred at 70° C. for one hour. The mixture is acidified with hydrochloric acid, and concentrated under reduced pressure to remove the methanol. The crystals are collected by filtration, washed with water, and dried to give 5-carboxymethyl-1-[4-(1-pyrrolidinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (142 g).

Workup

  1. stirringthe mixture is stirred at 70° C. for one hour
  2. concentrationconcentrated under reduced pressure
  3. customto remove the methanol
  4. filtrationThe crystals are collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-d421784bff0d4d558f0b52a8dd45f592
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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