Dimethylamine → HCID 21423148, compound

HRID 259124Notes

Reaction equation

HRID 259124 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 dimethyl 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 x), 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 x)
  6. customdried

Sources & evidence

ORD record
ord-3a0c78e5394043f6af21b6d8ecf02c04
Source dataset
uspto-grants-1977_07
Patent number
US04036842

Reaction notes

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