Methanol → 7-morpholino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-3-amine

HRID 1687010Notes

Reaction equation

HRID 1687010 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH2:10][CH2:9][C:8]=2[CH:20]=1)([O-])=O.CO>>[N:14]1([CH:11]2[CH2:10][CH2:9][C:8]3[CH:20]=[C:4]([NH2:1])[CH:5]=[CH:6][C:7]=3[CH2:13][CH2:12]2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 887MethanolHCID 67263703HCID 67263703, compound

Product 1

HCID 574161367-morpholino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-3-amine

Procedure

Into a Parr pressure reactor was added 4-(2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-morpholine (200 mg, 0.0007 mol) in methanol (6 mL, 0.1 mol). The reaction was placed under 40 psi for 10 h. HPLC indicated no starting material remaining. The reaction mixture was filtered through celite. The celite was further washed with methanol and DMF. The filtrated was concentrated in vacuo to a tannish-brown solid which was confirmed as product by both 1HNMR and LCMS. Material was carried on without further purification to give 7-Morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine. 1HNMR (400 MHz, CDCl3) δ 6.89 (d, 1H, J=7.8 Hz), 6.49 (s, 1H), 6.45 (d, 1H, J=7.8 Hz), 3.70 (broad s, 4H), 3.52 (broad s, 1H), 2.68-2.77 (m, 2H), 2.56 (broad s, 4H), 2.05 (m, 2H), 1.59 (broad s, 2H), 1.39 (m, 2H), 1.22 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washThe celite was further washed with methanol and DMF
  3. concentrationThe filtrated was concentrated in vacuo to a tannish-brown solid which
  4. customMaterial was carried on without further purification

Sources & evidence

ORD record
ord-0d1124fc362547fdbd7a7b66e65095a4
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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