1-Bromo-3-chloropropane → HCID 20284835, compound

HRID 127522Notes

Reaction equation

HRID 127522 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:11]=[C:10]2[C:6]([C:7]3[CH:15]([CH2:16][N:17]([C:19](OC(C)(C)C)=O)C)[CH2:14][CH2:13][S:12][C:8]=3[NH:9]2)=[CH:5][CH:4]=1.Br[CH2:29][CH2:30][CH2:31][Cl:32]>>[Cl:32][CH2:31][CH2:30][CH2:29][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([C:2]([F:26])([F:27])[F:1])[CH:11]=2)[C:7]2[CH:15]([CH2:16][NH:17][CH3:19])[CH2:14][CH2:13][S:12][C:8]1=2

Participants

3

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 20284772HCID 20284772, compound

Product 1

HCID 20284835HCID 20284835, compound

Procedure

By the same procedure as in Example 39(2), 7-trifluoromethyl-4-(N-t-butoxycarbonyl-N-methylaminomethyl)-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole (1.5 g) is made to react with 3-bromopropyl chloride followed by the reaction to remove the butoxycarbonyl group to give 9-(3-chloropropyl)-7-trifluoromethyl-4-methylaminomethyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole. Ethanol (15 ml) and a 50% aqueous solution of dimethylamine are added to the product. The solution is heated at 90°-95° C. in a sealed-tube for 8 hours and evaporated to remove the solvent. The residue is dissolved in chloroform and extracted with dilute hydrochloric acid. The extract is adjusted to pH 8 with an aqueous solution of sodium hydroxide and extracted with chloroform. The extract is washed with water, dried and condensed to give the title compound (1.28 g).

Workup

  1. customfollowed by the reaction
  2. customto remove the butoxycarbonyl group

Sources & evidence

ORD record
ord-fa970ad4391d406ba3d3fe0e91c53061
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Reaction notes

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