Hydrochloric Acid → 2-(3-(10,11-Dihydro-5h-dibenz[b,f]azepin-5-yl)-1-propyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid hydrochloride

HRID 1276408Notes

Reaction equation

HRID 1276408 reaction equation
C[O:2][C:3]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][N:6]1[CH2:15][CH2:16][CH2:17][N:18]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][CH2:21][C:20]2[CH:29]=[CH:30][CH:31]=[CH:32][C:19]1=2)=[O:4].C(O)C.[OH-].[Na+].[ClH:38]>O.O1CCCC1>[ClH:38].[CH:29]1[C:20]2[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:18]([CH2:17][CH2:16][CH2:15][N:6]3[CH:5]([C:3]([OH:4])=[O:2])[CH2:14][C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH2:7]3)[C:19]=2[CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 544781902-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid methyl ester

Product 1

HCID 699476182-(3-(10,11-Dihydro-5h-dibenz[b,f]azepin-5-yl)-1-propyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid hydrochlorideYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the above ester (0.80 g, 0.0019 mol), ethanol (5 ml), tetrahydrofuran (5 ml) and 4 N sodium hydroxide (4 ml) was stirred at room temperature for 22 h. Water (50 ml) and concentrated hydrochloric acid (2 ml) were added and the mixture was extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with brine (10 ml), dried (MgSO4) and concentrated in vacuo. This gave 0.8 g of a solid, which was triturated and washed with ethyl acetate (2×5 ml). Drying in vacuo, afforded 0.6 g (75%) of the title compound as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×20 ml)
  2. washThe combined organic extracts were washed with brine (10 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThis gave 0.8 g of a solid, which was triturated
  6. washwashed with ethyl acetate (2×5 ml)
  7. customDrying in vacuo

Sources & evidence

ORD record
ord-39ce146651d84ef78c2489ce4496107e
Source dataset
uspto-grants-2000_12
Patent number
US06166009

Reaction notes

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