Carbamic acid, ethyl ester → Hydrochloric Acid

HRID 1729716Notes

Reaction equation

HRID 1729716 reaction equation
NC(OCC)=O.C(OC([N:12]([CH2:15][CH2:16][CH:17]1[N:25]2[C:26]3[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=3[CH2:28][CH2:29][C:23]3=[C:24]2[C:19](=[CH:20][CH:21]=[CH:22]3)[CH:18]1[CH3:34])[CH2:13][CH3:14])=O)C.[Cl:35]C(OCC)=O.[OH-].[K+]>O.C(O)C>[CH2:13]([NH:12][CH2:15][CH2:16][C@@H:17]1[N:25]2[C:26]3[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=3[CH2:28][CH2:29][C:23]3=[C:24]2[C:19](=[CH:20][CH:21]=[CH:22]3)[C@H:18]1[CH3:34])[CH3:14].[ClH:35]

Participants

8

Reactant 4

HCID 5641Carbamic acid, ethyl ester2×HCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 21500415HCID 21500415, compound

Product 2

HCID 313Hydrochloric AcidHCID 86734118HCID 86734118, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

11.3 g (0.0298 mol) of the urethane, 1-[2-(N-ethoxycarbonyl-N-ethylamino)-ethyl]-1,2,6,7-tetrahydro-2-methylindolo[1,7-ab][1]benzazepine obtained after three successive treatments with ethyl chloroformate, were autoclaved for 8 hours at 140° C with a solution of 5.9 g [3 equivalents] of potassium hydroxide in 5.9 ml of water and 53 ml of ethanol. The resulting mixture was worked up as described in part B of Example 2 to yield the basic product, together with some unhydrolysed urethane which was given a second treatment with alkali. The combined basic products were distilled to give 5.9 g (64.7% yield) of pale-yellow, syrupy trans-1-(2-ethylaminoethyl)-1,2,6,7-tetrahydro-2-methylindolo[1,7-ab][1]benzazepine (boiling point 140° C [air-bath temperature]/2 × 10-5 mm Hg) whose hydrochloride melted at 169°-171° C.

Workup

  1. customto yield the basic product
  2. distillationThe combined basic products were distilled

Sources & evidence

ORD record
ord-5c9f21f175934974a7ff3b4d9eee5a91
Source dataset
uspto-grants-1976_11
Patent number
US03989717

Reaction notes

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