Sodium Iodide → n,n-Dimethyl-2-(7-nitro-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)acetamide

HRID 1262449Notes

Reaction equation

HRID 1262449 reaction equation
N[C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[N+:19]([O-:22])(O)=[O:20].[N+](C1C=CC2CCNCCC=2C=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+].ClCC(N(C)C)=O.[I-].[Na+].CN(C=O)C>>[N+:19]([C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1)([O-:22])=[O:20]

Participants

7

Reactant 6

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 574161402-(7-Amino-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)-n,n-dimethylacetamideHCID 855770687-Nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine nitrate

Product 1

HCID 57416161n,n-Dimethyl-2-(7-nitro-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)acetamideYield 56%

Conditions

Temperature
60 °C

Procedure

2-(7-amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide Into a round bottom flask, 7-Nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine nitric acid salt (3.80 g, 0.0149 mol), Potassium Carbonate (6.22 g, 0.0450 mol), 2-Chloro-N,N-dimethyl-acetamide (2.30 mL, 0.00224 mol), Sodium Iodide (2.28 g, 0.0152 mol) and DMF (60 mL, 0.8 mol) were added. The mixture was heated at 60° C. overnight. The reaction was partitioned with EtOAc and washed with Water (2×). The organic was separated, washed with Brine, and dried over Sodium Sulfate. The solid was filtered and washed with EtOAc. The solvent was removed under vacuum. The product was isolated via ISCO column chromatography with DCM and Methanol as eluant (0 to 10% Methanol). The collected fractions afforded 2-(7-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide as an orange solid (2.31 g, 56%). MP 102-104° C. LCMS (E/I+) 278 (M+H). NMR 1H (CDCl3)-7.95 (m, 2H), 7.24 (d, 1H, J=7.76 Hz), 3.34 st, 2H), 3.12 (s, 3H), 3.03 (m, 4H), 2.97 (s, 3H), 2.76 (m, 4H).

Workup

  1. customThe reaction was partitioned with EtOAc
  2. washwashed with Water (2×)
  3. customThe organic was separated
  4. washwashed with Brine
  5. dry with materialdried over Sodium Sulfate
  6. filtrationThe solid was filtered
  7. washwashed with EtOAc
  8. customThe solvent was removed under vacuum
  9. customThe product was isolated via ISCO column chromatography with DCM and Methanol as eluant (0 to 10% Methanol)

Sources & evidence

ORD record
ord-d7673969aaa54f6584a8227c998b1e0f
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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