Dimethylamine → HCID 21423148, compound

HRID 2397284Notes

Reaction equation

HRID 2397284 reaction equation
[CH3:1][C:2]1([CH2:19][C:20]([OH:22])=O)[C:7]2[NH:8][C:9]3[C:10]4[CH2:18][CH2:17][CH2:16][CH2:15][C:11]=4[CH:12]=[CH:13][C:14]=3[C:6]=2[CH2:5][CH2:4][O:3]1.[CH2:23]([N:25](CC)[CH2:26]C)C.ClC(OCC)=O.CNC>O1CCCC1>[CH3:23][N:25]([CH3:26])[C:20](=[O:22])[CH2:19][C:2]1([CH3:1])[C:7]2[NH:8][C:9]3[C:10]4[CH2:18][CH2:17][CH2:16][CH2:15][C:11]=4[CH:12]=[CH:13][C:14]=3[C:6]=2[CH2:5][CH2:4][O:3]1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 21423123HCID 21423123, compound

Product 1

HCID 21423148HCID 21423148, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1,2,3,4,7,8,10,11-Octahydro-10-methylbenzo[g]pyrano[3,4-b]indole-10-acetic acid (4.5 g), described in Example 69, is suspended in anhydrous tetrahydrofuran (120 ml), triethylamine (4.2 ml) is added, followed by dropwise addition of ethyl chloroformate (2.14 ml) at -5° C. After stirring for 105 minutes at 0° C., the solution is added dropwise at 0° C., to a stirred solution of 40% aqueous dimetyl amine (62 ml). After 2 hr. at room temperature, the tetrahydrofuran is evaporated and water added. The mixture is extracted with chloroform, the organic solution washed with water (2 ×), dried and taken to dryness to give the title compound, m.p. 176° - 178° C., νmaxCHCl3 3360, 1630 cm-1. This compound exhibits antibacterial activity.

Workup

  1. waitAfter 2 hr
  2. customat room temperature, the tetrahydrofuran is evaporated
  3. additionwater added
  4. extractionThe mixture is extracted with chloroform
  5. washthe organic solution washed with water (2 ×)
  6. customdried

Sources & evidence

ORD record
ord-79044761706c4a07a3aefe552b7da512
Source dataset
uspto-grants-1977_05
Patent number
US04021451

Reaction notes

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