Chloroacetyl chloride → 2-Chloro-N-[(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]acetamide

HRID 647592Notes

Reaction equation

HRID 647592 reaction equation
[CH3:1][C:2]1([CH2:15][NH2:16])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.C(N(CC)CC)C.[Cl:24][CH2:25][C:26](Cl)=[O:27]>O1CCCC1>[Cl:24][CH2:25][C:26]([NH:16][CH2:15][C:2]1([CH3:1])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:27]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 127081811,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-methanamine

Product 1

HCID 127081932-Chloro-N-[(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]acetamideYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indole-1-methanamine(15 g, described in Example 11), triethylamine(7 g), chloroacetyl chloride (7.9 g) and tetrahydrofuran (300 ml) is stirred at 0° C. for 5 minutes and at 25° C. for 18 hours, filtered and evaporated. The residue is crystallized from chloroform-diethyl ether to obtain the title compound (13.7 g); mp 186°-187° C.; nmr (CDCl3) δ3.41(d), 3.61(d), 3.89(m), 4.09(s), 6.75-7.50(m) and 8.0(t).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue is crystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-d9e0ed4319bb4b359aaa8d9de3f554e2
Source dataset
uspto-grants-1983_10
Patent number
US04409224

Reaction notes

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