Hydrochloric Acid → HCID 20304764, compound

HRID 2052302Notes

Reaction equation

HRID 2052302 reaction equation
[Cl:1]CCC(Cl)=O.[NH2:7][C:8]1C=[CH:14][CH:13]=[CH:12][C:9]=1CO.Cl.[NH:17]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][O:21][CH2:20][CH2:19][CH2:18]1>CCOCC.C(N(CC)CC)C.O>[ClH:1].[CH2:18]1[CH2:19][CH2:20][O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]3[C:9]4[CH2:8][NH:7][CH2:14][CH2:13][C:12]=4[N:17]1[C:24]=23

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 214392-Aminobenzyl alcoholHCID 693643-Chloropropionyl chlorideHCID 20304751HCID 20304751, compound

Product 1

HCID 20304764HCID 20304764, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2.54 g of β-chloropropionyl chloride in 30 ml of anhydrous ether is added slowly to a stirred solution of 2.13 g of 2-aminobenzyl alcohol in 100 ml of anhydrous ether and 1.8 ml of triethylamine previously cooled to 0° C. After the addition is complete, stirring is continued for another hour, keeping the reaction mixture at 0° C. Water (30 ml.) is then added, and the reaction mixture is acidified with hydrochloric acid. The ether layer is separated, washed with an aqueous saturated solution of sodium chloride, dried with sodium sulfate, filtered and evaporated to dryness. The resulting 2-(2-chloropropionamido)benzyl alcohol is converted, in a manner similar to that described for the preparation of 1,2,3,5-tetrahydro-4,1-benzoxazepine (E. Testa and L. Fontanella, Fr. Pat. No. 1,405,271) to 1,3,4,6-tetrahydro-2H-5,1-benzoxazocine. The latter, by a procedure similar to that described in Example 110 is converted to the title compound.

Workup

  1. additionAfter the addition
  2. waitis continued for another hour
  3. customat 0° C
  4. customThe ether layer is separated
  5. washwashed with an aqueous saturated solution of sodium chloride
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customthat described for the preparation of 1,2,3,5-tetrahydro-4,1-benzoxazepine (E

Sources & evidence

ORD record
ord-a4f53499b8a24436a9bf122fdc1a3bd1
Source dataset
uspto-grants-1980_01
Patent number
US04183936

Reaction notes

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